Supreme Court Set To Hear Landmark Online Sales Tax Case (gizmodo.com)
An anonymous reader quotes a report from Gizmodo: On Tuesday, the U.S. Supreme Court will hear arguments in a case that could at least somewhat clarify Donald Trump's complaints about Amazon "not paying internet taxes." It will also decide if those cheap deals on NewEgg are going to be less of a steal. The case concerns the state of South Dakota versus online retailers Wayfront, NewEgg, and Overstock.com in a battle over whether or not state sales tax should apply to all online transactions in the U.S., regardless of where the customer or retailer is located. It promises to have an impact on the internet's competition with brick-and-mortar retailers, as well as continue to address the ongoing legal questions surrounding real-world borders in the borderless world of online.
Wtf is wayfront? Was the editor trying to type Wayfair?
Regressive taxes ought to be illegal anyway. There's really no good reason for them to exist, only bad ones.
Any sufficiently unpopular but cohesive argument is indistinguishable from trolling.
" The #AmazonWashingtonPost, sometimes referred to as the guardian of Amazon not paying internet taxes (which they should) is FAKE NEWS!
— Donald J. Trump (@realDonaldTrump) June 28, 2017"
Presumably the tweet that this will clarify? But it's clear enough already, Trump is pissed at Bezos for owning Washington Post, and attacks Amazon because Bezos is the CEO. He doesn't even disguise the motive here.
What Trump's done of course is make any attempt to attack Amazon using the Executive powers open to court challenge. He cannot use executive powers to attack political enemies.
And what Trump's failed to do, was to get the Washingtom Post to censor its criticisms of Trump in exchange for not attacking Amazon. Hence the attacks continue.
Fundamentally, the justification for the tax is that it costs money maintaining the infrastructure and system that facilitates said sale. When the sale happens at a distance... both locations bear the burden, so.... both locations could reasonably demand sales tax. Sender's sales tax vs state's sales tax. Of course, this is handled internationally with customs, fees, import taxes and such, and the fed is specifically tasked with removing that sort of barrier to trade between states. And rightly so. And it doesn't sound so great as now we would then get two bodies slapping on their own sales tax. And it complicates the whole affair. A whole lot of affairs as every PoS system would need updating. There's a legit argument that this broad of a change would cause "undue burden". We're simply locked into the old way.
But it's not like reason has any real impact on what happens in court. So all that is probably moot.
South Dakota wants everyone else to obey their sales tax laws, whether or not they're located in South Dakota, while at the same time benefiting from usury laws not being enforceable across state lines. There's a reason most credit cards in the U.S. are issued from child corporations in South Dakota: South Dakota allows effectively unlimited interest rates on credit cards. They're perfectly fine with state-by-state enforcement when it benefits them.
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This would throw out the interstate commerce clause of the US constitution. Slippery slope, but it wouldn't be the first time.
jock tax level will each state with shipping places also want there own cut?
Was that word salad supposed to mean something?
I am guessing Joe had a stroke at the beginning of his post.
If SD wins, the first question every one of those online merchants will have for them is "What's the contact point for authoritative real-time-response data on what the applicable tax rate is for any address in South Dakota?". Because if SD expects those retailers to collect sales tax, SD has to be able to tell those retailers what tax they should collect for any given transaction. For a physical retailer it's easy, the tax is determined by the retailer's physical location and the buyer's address is irrelevant. SD's proposed scheme isn't nearly so neat and tidy, and why should it be the retailer's responsibility to figure out SD's mess for them?
And no, ZIP code isn't sufficiently granular for some places. I know places where there are 2 and sometimes 3 sales tax rates within the same ZIP code because that ZIP code spans local borders (half the ZIP code's within a city and collects city plus county in addition to state sales tax, the other half lies outside the city limits and collects only county and state sales tax, and one corner of what's within the city is within an additional tax district while the rest isn't).
After SD sorts that question out, the next one will be "OK, so now that we've collected the taxes, who do we talk to at your end to get the authoritative list of where to send the checks to for each taxing authority and the determination of which taxing authorities are owed taxes at what rate for each transaction?". Followed soon by "We appreciate the amusement value of the gibbering noises and screeches, but serious guys if you want us to remit your money you need to tell us how much to remit to who.".
Perhaps the Flying Spaghetti Monster sees it fit to give liberals a consolation price for loosing the chance to break the nearly 50 years of conservative majority in the Supreme Court
Small business on line sales. There are over 9000+ individual taxing districts in the US. Each requiring quarterly or if your sales are small yearly reports filed.
;)
Each one is different, each one has it's own crazy rules. Here is one in the state of Minnesota. Say we sell a pair of gloves. If the user uses them to keep their hands clean they are taxable. If the user uses them for a safety purpose. handling glass with sharp edges, they are not taxable. How does the seller know? So they always tax!
The entire sales tax code, nation wide in the 1000s of taxing districts are a fuddled mess of crap.
Big online sellers like Amazon are all for it, they want to force all small independents in to Amazon stores where they skim 8% - 15% off the top of all invoice.totals as their cut.
Amazons master inventory system is a complete mess. They are always moving your products from the lower groups in to the 15% cut group. You call them up argue with them for a week and they will move that product back to the proper group. Next week they move 2 more up, rinse and repeat.
If the government wants a sales tax they should be clear concise and honest. Just set one rate, one reporting entity, once per year settling up. Which they never do, everything government does is a complete convoluted morass of crap..
How is a one-two person small shop supposed to file sale tax reports in all 9000+ taxing districts? Let alone quarterly reports/payments.
This will go through because the big operators want to force all the small online retailers to pay them a cut.
You may ask how I know, I run a business, have a state sales tax number. I also support other online sales sites from a tech stand point. I am in the trenches!
Just my 2 cents
jock tax level will each state with shipping places also want there own cut?
Well, not a best textile product but that own cut bumbles generously, no tax cut understated.
I also use spill chick.
HTH.
http://taxcloud.com
I don't respond to AC's.
You may ask how I know, I run a business,
You should probably try a bit harder, then. http://taxcloud.com
I don't respond to AC's.
It would be great if they win this case.
People could use digital stores to avoid taxes and reduce the power of the state.
Less corruption of society.
Thank you, Bradley Manning, Edward Snowden and so many others, for courageously defending humanity, my freedom and more!
that could at least somewhat clarify Donald Trump's complaints about Amazon "not paying internet taxes."
It doesn't matter as Amazon already collects state sales tax for every state that has a sales tax, unlike say...Trump's own business which only collects sales tax for 3 states. The only clarity needed for Trumps comments are: he's an idiot that doesn't know what he's talking about.
https://www.washingtonpost.com...
Fascism: An authoritarian and nationalistic right-wing system of government and social organization. See also: NAZI's
And computers do do that. That's why taxes are withheld from your paycheck.
Not good enough. There is genuinely zero reason why essentially the entire tax system could not be automated. Sure it would look a bit different than it does today but that's not a bad thing. 99% of it could be completely automated. For people with more complicated tax situations we have them file some paperwork but the vast majority of the public should never have to pay an accountant or a tax software company. I'm accountant and it's just not that hard.
But your employer can't possibly know about all your deductions or other income so the withholdings are sort of a guess.
Sure they can. You just have to tell them. Or tell the IRS directly for bits that don't concern your employer. Or we do away with the deductions and handle the taxes with a more rational tax system. One has to admit that the US tax system is more than a little bonkers.
...are not so cheap anymore. I was just hit with a tax bill from my state asking me to pay back taxes on purchases from NewEgg dating back to 2014, 2015 and 2016 based on "voluntarily reported" information that NewEgg has provided them. That is despite my state having a "internet use tax" that I have been paying since it was introduced and which is supposed to cover out-of-state purchases. I expect to see more of that happening from now on.
All of them (in practice). If you are rich, you don't pay sales taxes. You get tax credits and deductions for them. You are too poor to understand, or you'd already know that.
Well I'm an accountant and I'll disagree. Rich people pay sales tax too and it's easy to prove that they do. The difference is that sales tax amounts to a rounding error in their overall financial picture. A sales tax of 6% on groceries affects someone making $20K/year a LOT more than someone making $200K/year. Rich people don't get a special rich person discount at the grocery store or at the car dealership. In some they can run some expenses through a corporation which gets some deductions (not credits) but most of what they buy they pay sales tax on too, same as anyone else.
That's the stupidest argument ever. Yes, you aren't the first I've heard say that. If people, not corporations pay taxes, then my employer, a corporation, pays all my taxes, not any people.
Not only is that not a stupid argument, it's got a name and it's a well understood concept. It's called tax incidence and it's demonstrably correct. Let's use an example. If we tax gasoline sales the oil companies are going to be able to pass most or all of that cost to consumers so the party bearing the burden of that tax isn't the shareholders of the oil company but the car owners.
You should be in politics. Yes, that's an insult.
If you disagree with his argument fine but no need to be a dick about it.
You know lots of these rural people don't even know their physical location? That's not a joke. I deal with them every day. They have a P.O. Box for getting letters and they only know their physical location from rough driving directions. If you asked them to state the actual standard identifying information they couldn't tell you. Even the ones that can have disagreements about what city they are really considered a part of or if they are an address on the highway -- things that will definitely come into play when computing local taxes.
This is true. You'd basically have to have to use some sort of global coordinate system perhaps combined with a GPS to really make it work. Some parts of the world are actually doing something along those lines because street addresses have some pretty significant limitations.
My county has a 1% sales tax on the first $5,000 of a sale. If you spend $10,000 you only pay that 1% on $5,000 of that sale ($50 instead of $100).
I thought that was common.
If we follow this line of reasoning, were a state can force vendors and citizens located wholly in another state to comply with the first state's sales tax laws, why can they not be forced to comply with another state's gun laws, abortion laws, marriage laws, pollution laws, welfare laws, ...?
Not to mention that the items taxed are taxed differently in different states. Food may not be taxed at all in one state, but taxed fully in another.
For example, a bagel in NYC is not taxed, but a sliced bagel is taxed as prepared food.
In Washington, a candy bar containing flour (a Milky Way Bar or Kit Kat) is not taxed, while one without flour (a Milky Way Midnight Bar or 3 Musketeers) is. The only way for a consumer to know what's taxed before heading to the checkout counter is to read the ingredient label and the state's definition of "candy or candy-like products."
In Texas and other states, wigs and hairpieces may or may not be taxed, depending on whether the customer has a medical need for the fake hair (e.g. cancer treatments) or just wants a different look.
With 17,500 or so jurisdictions, each with weird exemptions, it would be a compliance nightmare.
Most states *already* tax internet and catalog purchases, indeed all purchases made out-of-state for goods brought into the state. They just currently cannot force merchants outside those states to comply and act as proxy tax-collectors for them.
These are called Use Taxes.
The thing is, States are upset that no one pays Use Taxes and now want to force businesses in *other states* into servitude as tax collectors.
What right does one state have to force a brick-and-mortar retailer in another state to collect sales taxes from border-crossing customers? None.
Why then should they be able to force an out-of-state retailer of the virtual sort to collect sales taxes from virtual border-crossing customers?
If I lived in North Dakota and I hopped across the border to Montana and bought a book at a shop there (no sales tax in Montana) then took it back with me to ND, I would be responsible for paying any use tax owed, not the book shopkeeper in Montana. Same rules should apply to the Montana shopkeeper if he mails my books to me at home.
This Streamlined Sales Tax idea is about allowing states to force businesses residing completely in *other states* to become proxy tax collectors, not to mention that those businesses will be forced into audits and liabilities from any state or tribal tax that can be passed completely without representation.
People act as if technology will solve these "problems"...the equanimity of sales taxes are not simply a matter of rates. A software database would be huge to encompass the differences between states. Consider that in NYC as bagel is taxable if sold sliced, but not taxed if not sliced. Or that candy in Illinois with a certain percentage of flour in its composition is food and not taxed, but no-flour candy is taxed.
The states say "hey, turbo tax will manage that for you," What happens when Cali, NY, Mass, and DC all decide to audit you in the same year?
What if you get a tax audit statement from Minnesota? You'll have to prove that you didn't sell anything to anyone in Minnesota...how do you prove that negative?
Brick-and-mortar Main Street vendors in Delaware have no obligation to collect and remit Maryland use taxes for Marylanders frequenting their stores. Even if the Marylanders are jumping across the state line to take advantage of Delaware's 0% sales tax. Even if the Marylanders then fail to report and pay their state's use taxes.
Internet vendors should continue to have the same right to not be forced into acting as a tax collector proxy for some state in which they do not have a physical point-of-presence.
While I suppose tax-and-spend supporters would like it, I think many people and Main Street vendors would be offended at the notion that a state like, let's say New York, could force a brick-and-mortar store in, say, Orlando, FL to quiz customers so as to ferret out the New Yorkers and collect the NY sales tax on any items purchased that might be possibly taken home to New York (and then subject to NY use taxes). But it would put the Orlando brick-and-mortar store selling to a New Yorker in the store in sync with what they want an Orlando online vendor to do for New York customers.
Even paying sales tax, I'd still come out ahead on most online purchases. I don't look at something online and say "uh oh, they charge sales tax, I might as well get in the car and buy it from some big box store".
Imagine a mom&pop store in a state with 0% sales-tax, say, Delaware. Further assume it is close to the border with a state that has a high sales tax, like, hmm, Maryland which has a 7% rate.
By reputation and the lure of 0% sales tax, people from Md make the short trip to mom&pop to buy their wares. Mon&pop do not care nor ask where their customers are from, there is no question *at all* where the transaction takes place. It is subject to Delaware sales tax: 0%. Being a brick-and-mortar store in Delaware, mom&pop charge all their customers no sales tax.
Mom&pop decide to create a website to allow their loyal customers (and hopefully new customers) to buy things online. Under this proposed rule mom&pop not only have to treat their online customers differently from their in-store customers, but have to comply with Md's tax regime (and by implication all the other tax regimes) as an unpaid tax collector? With all the liabilities, audit threats, and possible penalties?
Bear in mind that what are being discussed are sales taxes, which are paid by customers.
Businesses merely collect and remit these taxes. They are forced to act as proxy tax collectors because it is more efficient for states for force a few thousands of businesses to account for their sales than it is to force a few million citizens to do so individually (which is already a proven utter failure as per use taxes).
Please bear that in mind before going of on a "these online corporations are skipping out on taxes they owe! mom&pop brick-and-mortars are carrying their load!" chain of thought.
In a brick-and-mortar case, we know the location to use for the transaction as the entire transaction occurs between people located within a single state and subject to the laws of they state they are all physically in. So the state can force a store to collect sales tax from its customers who come into the store and make purchases.
For an online purchase, it's not so clear?
Purchaser's location? What if the purchaser is in a hotel room far from home, maybe even out of the country? Or on an airplane?
Shipped-to address for the purchase or Purchaser's mailing address? I foresee a lot of Montana mailing addresses once someone in Montana realizes the business opportunity inherent in sales-tax avoidance arbitrage.
Purchaser's home address? What if the item is shipped elsewhere, e.g. a gift to an aunt in a 3rd state? And why would I tell anyone my home address instead of my mailing address?
Sender's address? Which one, the HQ? The warehouse? The fulfillment center?
Will states be able to force out-of-state brick-and-mortars to quiz customers and collect and remit use taxes on the assumption that their citizens temporarily in another state just bought something that they *should* have bought at home, thus depriving the home state of revenue?
Illinois has a use tax. By order from California, you are obligated by the state use tax law to collect from yourself the corresponding Illinois sales tax and include it in your income tax filing.
Many Illinois taxpayers are unaware that a Use Tax exists in Illinois. Do you know about Use Tax?
In 1955, the General Assembly passed the Use Tax Act. Use Tax is a sales tax that you, as the purchaser, owe on items that you buy for use in Illinois. If the seller does not collect at least 6.25 percent sales tax, you must pay the difference to the Illinois Department of Revenue. The most common purchases on which the seller does not collect Illinois Use Tax are those made via the internet, from a mail order catalog, or made when traveling outside Illinois. You must keep your receipts when you make these types of purchases.
In 2010, the General Assembly passed a law making it easier for individuals to pay their Use Tax by putting a line on Form IL-1040.
SD citizens, like citizens in most states, generally are ignorant or simply ignore the states use tax laws.
SD is unsatisfied with the perfectly justifiable actions of simply attacking its citizens with audits for not not paying their use taxes and just think it would be easier and less likely to make their citizens angry by forcing out-of-state vendors to be SD sales tax collectors like they force SD vendors.
The issue here is, then what else can a state for out-of-state entities to do?
--------------
The South Dakota use tax is a special excise tax assessed on property purchased for use in South Dakota in a jurisdiction where a lower (or no) sales tax was collected on the purchase.
The South Dakota use tax should be paid for items bought tax-free over the internet, bought while traveling, or transported into South Dakota from a state with a lower sales tax rate.
The South Dakota use tax rate is 4%, the same as the regular South Dakota sales tax. Including local taxes, the South Dakota use tax can be as high as 2.000%.
The South Dakota Use Tax is a little-known tax that complements the regular South Dakota sales tax to ensure that purchases made outside of South Dakota are not exempt from the South Dakota sales tax.
Instead of taxing the sale of tangible property which takes place outside of South Dakota's jurisdiction (and thus cannot be taxed), the South Dakota Use Tax taxes the use or consumption of tangible property bought in other jurisdictions with a lower sales tax rate and brought back into South Dakota.
State of California Sales Tax How Do I Calculate How Much Use Tax I Owe?
If you made any purchases online or outside of South Dakota for which you paid less then South Dakota's 4% in sales tax, you are responsible for paying South Dakota a use tax on those purchases equal to 4% of the total purchase price less any sales taxes already paid to other jurisductions.
When Big Giant Orange Head took advantage of the tax code for his business, he defended the practice as "smart business". Now that he's Prez he calls Amazon a "tax cheat and extremely unfair". Gee BGOH, your attitude on what smart business is seems highly flexible and situation dependent!
A more likely explanation than anything you'll ever hear from BGOH's mouth: Tax avoidance by TrumpCo. is always going to be "good", because of self-interest. Tax avoidance by Amazon is always going to be "bad" because of Jeff Bezos and the Washington Post.
BGOH is pleasantly selfish, ego-driven and predictable.
I fail to see the difference between online purchases and mail order purchases. Mail order purchases have been taxed without any contention. What is the difference in the purchase is ordered by mail, phone or the internet?
Sales tax is not mine to pay. It's those that make the sale that are obligated to pay the tax, not the buyer.
The sellers have simply been getting away with it for so many decades. I simply will not pay a sales tax.
If states force online retailers to collect their sales tax - thus burdening the online retailer with knowing about all tax jurisdictions, having common descriptions of items country wide so you know what is even taxable and its particular rate on any given day then....
make all non-online retailers handle the sales tax rates the purchaser would pay at their home and remit them to their home states as well! You make a purchase, show your ID and then the sales tax rate will be whatever it would be for your home address. If you come from a state that is sensible and doesn't collect sales tax - you wouldn't have to pay it anywhere. If you come from a state that is nuts - then you're equally repressed everywhere in the United States you shop.
Seems fair to me. Your opinions will probably vary.
Come on Donny, could you at least TRY to know what the fuck you're talking about before you start flapping your gums like that?
Also could you grow the fuck up and accept that Jeff Bezos is just a better and more successful businessman than you are? Seriously.
Not long ago, a New York jeweler admitted to selling very expensive jewelry, giving it to the customer in the store and sending an empty box to their "home" address in another state with no sales tax. No money collected and all perfectly "legal."
A few years ago, it was the auction houses, selling paintings worth millions and then "sent" to their "vacation homes" in a sales tax free state.
Oh, and if you go to work and are told what to do, you do not pay any taxes at all. All of your taxes are paid by your employer. After all, that is where the money comes from. This is just a ploy to make you think you are earning more money than you actually are, to keep you quiet and calm.
There's a good piece in the WSJ about this and the insanity of it all. In one tax district, a Twix bar is taxed at a different rate than a Snickers bar because one of the ingredients in a Twix bar is flour. Snickers, on the other hand, is considered candy. Nobody but outfits as big as Amazon could comply with all the taxation because only they have the army of people necessary to deal with it.
I, myself, have to deal with the paperwork nightmare in different states and different government agencies. It takes up so much time that I'm seriously considering tacking on a "Document preparation fee" to every invoice that requires me to fill out some stupid form e.g. the DPRC (aka The State of California) that to this day makes vendors sign a form that says "I swear on my life that I don't do business in Darfur".
Whose tax system? No seriously that's the fundamental flaw in anyone thinking their tax system can be automated completely. There is no agreed international tax system or transfer of private information between countries.
I'm worried about the country I live in so let's start there. Don't make perfect the enemy of good. The vast majority of the public could/should have their taxes automatically collected through their employers. Get rid of most of the complicated deductions and viola - life is simpler with no tax deadline stress.
That I agree with. I have income in multiple countries, depreciating assets in multiple countries, shares in multiple countries some subject to deferral schemes, and my own business on the side.
That makes you wildly outside the norm. For guys like you then we can have some extra paperwork and that's probably fine. You obviously can handle it. But even for you some amount of your taxes probably could be automated more than it is.
Tax the purchase at the location of the item. That's how it should be. If I drive to another city in my home state that has a higher sales tax than my hometown, I can't demand to pay the lower rate because of where I live. Sales are taxed where the transaction takes place in brick-and-mortar stores. Keep it that way for online purchases.
Let the states, counties, and cities compete to lure internet businesses to their locations. The ones with low sales tax would have an edge on the ones with outrageous tax rates. For a company like Amazon that has warehouses in a bunch of states, tax the item at the warehouse location that it's shipped from.
Local governments probably wouldn't like it that way, but I would remind them that 5% of something is always more than 10% of nothing.
Some states also make this hard to file even if you as an individual wanted to, for example my state used to be setup where you needed an EIN (Employer Identification Number) to pay Use Tax.
They also wanted Use Tax to be pre-paid on a quarterly basis.
Needless to say most people did not go through the headaches/hoops to pay it.
They recently made a change where individuals can account for Use Tax when filing the yearly State Income Tax, very much easier and I know it made my life easier as far as paying the Use Tax.
Most states *already* tax internet and catalog purchases, indeed all purchases made out-of-state for goods brought into the state. They just currently cannot force merchants outside those states to comply and act as proxy tax-collectors for them.
These are called Use Taxes.
The thing is, States are upset that no one pays Use Taxes and now want to force businesses in *other states* into servitude as tax collectors.
Use taxes on individual have ALWAYS been a Bill of Rights violation. The government can not require individuals to keep track of all their purchases, and whether or not sales tax was paid, and whether or not additional tax is paid - nor can it require individuals to provide details of their purchases to the government in an audit. All of that is illegal. A use tax is a violation of a number of rights arising under the 9th and 10th Amendments - you can look up the details in prior discussions on this topic on this forum.
Notice I said individuals, meaning living human beings. The rules could potentially be different for businesses. Large businesses often have accountants and lawyers permanently on hire, formal accounting procedures, and some expectation of public accountability which would require tracking their purchases and having that information available for accounting audit. A use tax would be very harmful to small businesses, of course. So on the whole, it wouldn't be a good idea to have a use tax on businesses - but it isn't outright illegal.
Whether or not they understand the legal details, people understand that this is not a legitimate exercise of government authority, which is why they don't comply with the illegal laws. Indeed, public non-compliance creates a presumption that a law is violating some right retained by the people - which should have provided a clue to government long ago that it was breaking the law, and a government with competence and integrity would have changed its policies.
In practice, government in the USA (federal, state, and local) has learned that it can get away with illegal conduct, because it takes years of time and millions of dollars to fight it, so in most cases only the battles the rich care about get won. The laws are not maintained properly - lots of illegal stuff gets written into the codes, and not removed for many years, if ever. The long history of the illegal Jim Crow laws is not anything exceptional - that sort of thing happens all the time. As a result, government in the USA (again, this happens at all levels of government, not just the federal) violates the Bill of Rights on a routine basis (the Nuremberg Precedent might as well never have been created).
There is always the possibility that enough public attention will be attracted to an issue for long enough to undo or partly block the illegal activity (as happened with the Jim Crow laws), but the odds on that happening for most issues are low as there are lots of distractions for public attention (and there are major problems with the US educational system, so many people don't have the education to understand many issues). The fact that the rich (on the whole) don't care about the sales tax issue (regressive taxes are just fine in their minds, the existence of any regressive tax means the rich end up paying less in taxes) is part of the reason why this particular issue has dragged on for so long.
The vast majority of the pricing difference between online venders and local is far more than the sales tax amount, so the tax issue really isn't a question of consumers saving money. However, if the government can be influenced into making individual consumers track their purchases (to be legal, this would require a Constitutional Amendment - as mentioned before, legality as such has not been a government priority in recent decades), this will be such an enormous headache that it will effectively kill the majority of the Internet economy. It will destroy the primary source of economic growth for the past few decades - an
Even paying sales tax, I'd still come out ahead on most online purchases. I don't look at something online and say "uh oh, they charge sales tax, I might as well get in the car and buy it from some big box store".
Exactly - this whole issue is not about the cost of the goods.
But if they can make it a real hassle for the consumer to report taxes on everything you buy, then you might not be so inclined to buy remotely, so the brick-and-morter stores have an interest in making the law as screwed up as they can get it (even if that violates fundamental rights). It might destroy the Internet - but it would certainly cripple Internet commerce.
Politicians, of course, want to maximize their budgets so they can spend that money on things that will get them re-elected, and acting within the legitimate authority of government is only something they have to pretend to care about. After all, when was the last time a politician received anything other than a slap on the wrist when they implemented or enforced a law in violation of the Bill of Rights (practically a daily occurrence)?
Finally, most of the wealthy want to maximize the government's income from any and all forms of regressive tax, since the the larger the percentage of government budget paid by the public in the form of regressive taxes, the less money the rich have to pay through progressive taxes.
So we have three amoral special interest groups operating here.
In the USA, special interest groups try to get their way by bribing politicians and by hiring lawyers and other lobbyists to create the illusion that their interests should be furthered - even though this is usually at the expense of society.
Some of the wealthy are invested in internet business, or are smart enough to realize why this is a really bad idea overall, so there's two sides to this matter.
There's also a fundamental Bill of Rights issue here, at least to respect to collecting from individuals, but given the track record of government in the USA, they'll probably do everything they can to ignore that and pretend it doesn't exist (along the lines of The Emperor's New Clothes: if you pretend something isn't true, then it isn't - if the government pretends it's not actually breaking the law, then perhaps nobody with the power to make a difference will say anything).
So ultimately this will come down to not a matter of law, but rather which special interest groups can spend the most money on lawyers.
Invest in America, buy a politician and a bunch of lawyers. It's pathetic.