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I've been a contractor and consultant for many years and I've had to provide my own insurance for many years.

COBRA = Up to 18-months at Full Corporate & Personal Payment + ~2% Administrative Fees

Just to let you know that coverage under COBRA is not always good since you have to pay your part of the premium, the company's part of the premium, and also an added administrative fee so you're paying an additional premium for coverage that is now costing you twice or much more.

Independent Coverage from Major US HMO (Aetna, Oxford, Blue Cross/Shield, etc.) = $1,400 - $1,800 per Month

For shits and giggles I decided to call and research the major insurance companies in New York state in the US and ask them about what it would cost to cover me individually and I got quote from $1,400 to $1,800 for the lowest priced HMO prices for a fully healthy 25-30 year old male, non-smoking, non-drinking, no-preconditions. These prices were direct from the provider themselves and I was surprised that they quoted me so much above what the New York State Insurance Department for Health Care Plans had listed on their web site.

Freelancers Union or Local Chamber of Commerce

Be aware that the health plans offered at least in New York State around the mid 2005's by the FreelancersUnion.org were not exactly cheap nor good, they offered HIP HMO which was the lowest rated HMO with the higher complaint count according to the NYS Insurance Department for Health Care Plans and they wanted $700 for individual only and over $1,000 for family. HIP had a series of corruption and accounting issues that were public and incompetence that wasn't but was know by folks that worked there, some were friends.

They did offer a pretty good "discount" plan for Dental by Guardian for ~$50 per month that did have pretty good rates for procedures, such as %50 off for a root canal and crown, and really low costs of $12 for composite molar fillings with multiple faces being done.

Now Freelancer's Union has expanded and they offer PPO 1,2,3 (Preferred Provider Organization = You pick your own doctor not from an HMO network) that are damn expensive at $300-500 for individual or $800-1,400 for family and HD $5K and $10K (High Deductible ~= Catastrophic Health Problem) plans that are still quite expensive at $200-300 for individual or $550-900 for a family.

I've been with and have used Freelancer's Unions dental plan but not the health plan and I did think that they offered such a great deal and savings. Their plans are expensive and they are not really a union they are a for-profit company that is just reselling you insurance! They do not run their business very efficiently or very well with multiple cases of screw ups every year when it comes time to renew the plans and select your new plans, such as two years ago when they didn't do re-enrollment for a whole month after the deadline since they screwed up. They run a fully paperless frontend for you but from the back office work they must deal with reams of it. Just be careful and weary of this so called "union" since they are not one!

Uninsured Option!

I decided to give up on HMO or PPO health insurance because it's just too insanely expensive at $900-$1,400 for coverage. That is more money that my biggest expense that is rent. It is an insane amount of money for a self-employed individual making due with a few clients and non-steady income.

The United States is a horrible place to live without be subservient to a corporation who holds their benefits and insurance plans over you like an indentured servant since if you start and family and decide to leave their good graces or are no longer desired you're in the path of bankruptcy for even non-lethal health problems or accidents.

Small group insurance isn't much better than the individual market.
The OP's best bet is to take advantage of COBRA, as s/he is still employed. By law, you can only be charged a 2% administrative fee over the cost your company pays for the plan. COBRA covers Medical, Dental, Vision and even your FSA plan. An alternative is to look into something like the Freelancers Union
A friend looking coming close to the 18 month mandatory limit of COBRA (most people) , took an admin job for the benefits, stayed long enough to begin coverage and eligibility for COBRA, and quit. It reset the clock and he is now eligible for COBRA through the new plan.

or move to canada!

FYI, in the U.S., you can buy health insurance at a discount by joining either a freelancer's union or your local Chamber of Commerce. I did the latter when I was freelance. Most CoC's offer health insurance packages to their members at group rates, e.g. lower than what you'd pay directly. Still expensive, though. You definitely need to factor that into your budget.

For independent contractors or freelancers, a more comparable model might be the Freelancer's Union or an entertainment guild/mutual aid association like yours truly's union.

Both use collective bargaining to obtain health benefits and provide common resume writing/promotion/education/development services; the latter is a proper union has wage/working condition bargaining power by having a master agreement with all employers in a jurisdiction.

A union of freelancers is workable, and is the SOP in the film/television industry, when union benefits are made "portable" from job to job. In this case then the union's main job is to provide continuity of benefits, so I don't end up having six 401k's all over Los Angeles and paying COBRA one month out of every five.

http://www.freelancersunion.org/index.html

There are unions FOR US.

NEVER join "steelworkers" unless you want to be bullied by "your side" as much as you've been bullied by "the other side".

Not particularly coherent today, so forgive me if not everything makes sense, but I'll take a shot at replying.

http://www.freelancersunion.org/

What they do, except perhaps with more of a music slant. Like offering discounts to equipment/promotional resources or pairing producers with singers, etc. If done right, it could theoretically completely replace what the RIAA does. RIAA members owning a good chunk of the major media outlets does present a challenge to the organizers of such a union, the RIAA could be driven to extinction by this alone even without the internet.

Add the internet as a viable alternative promotion channel to more traditional forms of media, and it might actually fly.

Ironic thing is, this model would bring the music industry far closer to a free market than one that involves the RIAA. That is, assuming the union leaders aren't eventually corrupted by the money. After all, the music industry is huge.

Check it out:

http://www.freelancersunion.org/

They started this in New York for people in just your situation.

I have no idea how good they are but I often see ads here in NYC for Freelancers Union, it looks like something that could help you. Good luck!

1) Health Insurance

check out the Working Today Freelancer's Union. They offer Individual and Family Health & Dental Insurance plans for freelancers in tech-related jobs in the greater NYC metropolitan area.

1) Health Insurance

check out the Working Today Freelancer's Union. They offer Individual and Family Health & Dental Insurance plans for freelancers in tech-related jobs in the greater NYC metropolitan area.