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I don't even try to write it down, too easy to miss something.
I install Belarc Advisor, which is a free (as in beer - for personal use at least) program that catalogs your installed software and finds product keys for many programs automatically.
Print the report that it generates, highlight any really important items, (make sure you have the installers before you format) and just format and reinstall.
Usually makes the job relatively painless.

or use a program that will actually give you some info on what it does before you sign up for the program

http://belarc.com/

(note belarc Advisor is free for personal use)

I would add: Document everything. Save any emails about software installations, make a spreadsheet contains: Name of Software, Key used, Installed on, Requested by.

Check out Belarc Advisor for Windows machines. :)

I never hesitate to violate an EULA since an EULA is worthless. Ever since I read the suggestion on here I have always amended such contracts with a post-it on the monitor to read "Right of first sale applies" and then click agree. I have the right to amend any contract prior to signing it. However, I don't and won't infringe on the copyright. Making backups and storing the original away or installing it twice on one PC for a dual boot is one thing, but installing it on 20 machines is entirely different.

well as far as your keys are concerned hit http://www.belarc.com/ and download Advisor

your missing media problem is also solveable via the obvious methods (why is the Rum always gone???)

I'm really surprised no one has yet mentioned what we use in our IT department, the Belarc Advisor, a free download at http://www.belarc.com/free_download.html. It scans for all software, regardless of open source or not.
"The Belarc Advisor builds a detailed profile of your installed software and hardware, missing Microsoft hotfixes, anti-virus status, CIS (Center for Internet Security) benchmarks, and displays the results in your Web browser. All of your PC profile information is kept private on your PC and is not sent to any web server."

"Most people moved from Windows 98 to XP. They gained a much more secure system in that move and moved to the proven NT kernel from the 95/98/ME codebase. The move to Vista? I see little gain but eye candy" - by LWATCDR (28044) on Wednesday May 16, @11:45AM (#19146299)

Ok, then quantify it, for yourself, by running these tests: Run the CIS Tool 1.0, OR, Belarc Advisor (both are security benchmarks, the former moreso than the latter) from here:

CIS Tool 1.0

http://www.cisecurity.org/bench_windows.html

&/or

Belarc Advisor

http://www.belarc.com/

Over Windows 2000 or Windows XP first (in their stock configuration), and then Windows Server 2003. Then, fully patch them even, and see your results. Mind you, you CAN score higher if you take the time to hand-harden them, ALL of them, for better security (via various settings and registry hacks).

Windows 2000 and Windows XP (and yes, even Windows Server 2003) won't score as secure as does VISTA out of the box on that test, no questions asked.

(I know this, because I ran such a test @ techpowerup.com forums using a FULLY CUSTOM HAND-TUNED/TWEAKED SECURED Windows Server 2003 SP #1 & SP #2 vs. VISTA (yes, I did better than VISTA did "out-of-the-box" using its predecessor and direct ancestor in Windows Server 2003 SP #1 & SP #2 than VISTA did, but NOT OUT OF THE BOX!))

See these URL's for my test results prior to you running your own tests using these tools for security analysis:

http://forums.techpowerup.com/showthread.php?s=74b 140c83efbebf0895ce198e8d33125&t=25428&highlight=CI S+Tool

and

http://forums.techpowerup.com/showthread.php?t=268 18

VISTA was far more secure, as-is/out of the box, than any of them (Windows 2000/XP/Server 2003) did initially (w/ out hand tweaking via registry hacks & more) for security.

APK

P.S.=> My current score using a hand-tuned/tweaked hardened build of Windows Server 2003 SP #2 scores an 84.735 on CIS Tool 1.0... apk

If the machine is any kind of functional before you get started, you can run Belarc Advisor to fish the Windows and Office product codes out of the registry. I don't care what was there before, those are the numbers I type back into the boxes when I have to reinstall. I see numbers from Belarc that match the ones on the sticker maybe 2/3s of the time. I'm not sure what happens the other third, and to be honest it's none of my business.

A co-worker of mine and I were discussing this very issue yesterday. I surmised that Boot Camp will actually increase Windows XP piracy. There's a resonable assumption that many Mac users will have access to some sort of Windows XP disc, and finding a Volume License key to avoid registration is not hard at all. Hell, if you work for a large company, run Belarc Advisor on your corporate box and you probably have the VL key there staring you in the face. If you're a developer, chances are you have MSDN-granted VL keys with your subscription. Ask your neighbor's teenager to find one for you if those don't work.

The bottom line : I can't see people spending $200-300 for a license of Windows XP just to dual-boot on their Mac. Sure, you'll have the Boy Scouts out there that will fork over the cash, but I bet you'll find most people end up installing a not-100%-legal copy of Windows XP on their Intel-based Macs.

Or, run Belarc and get ALL your license keys in one handy HTML file, and a list of all the software on your system, and model numbers and serial numbers of some of your hardware, and...

For everything else there's Mastercard....?? No, Everest.

I have a Mac. My mum has a Mac. I have a Wintel box, but's got Win95 installed, and I generally vacuum out the dustbunnies before booting it. My mum hears tales of woe from her bridge-playing cronies about 'worms' and 'viruses' and 'my computer broke, and I have a man in once a month to clean it up, how about you', and after two years still doesn't quite understand what's going on well enough to have developed MacOSX smugness.

[1] Installing *on* Windows? Generally by the time I get called in, any machine I get to see is so smashed by viruses, worms, spyware, descents into DLL hell and so on, that the fastest way to clean it up is to back up, wipe, and reinstall. Sometimes I add a bigger hard disc.
(Tip: Ma/Pa has probably lost their Windows CD key. I found you can get these back using Belarc Advisor, http://www.belarc.com/ -- but this won't help unless Ma/Pa still has the original CDs.]

[2] Ad-Aware SE is my favourite spyware killer -- http://www.lavasoftusa.com/

I also generally nag about keeping antivirus software up-to-date, and also point out how many ways their USB ADSL modem can stop working; far better to fit an ethernet card if necessary, and get a combined modem/router/hub/hardware firewall. But I'm usually flogging a dead horse by this point.

It's likely a driver issue. XP loads numerous hidden kernel drivers at boot time. Some of these are not the usual device driver. Sometimes they could be ones for the personal firewall or antivirus. Heck, even Belarc Advisor loads a kernel driver. You can see what's loaded by typing

sc query type= driver

Belarc offers a free PC audit tool that I have found VERY useful in trying to discover exactly what h/w and s/w a user has installed. And it free.

I always evaluate licenses before I download things at work. I have a linux box where just about everything is GPL, and on my (xp) laptop, I can run Belarc Advisor to see what I have installed. This keeps me and my company out of hot water. I'm probably more laxed at home. In fact, only thing I can think of on my work machine that is commercial that wasn't given to me by work, is X-Win32, which I purchased a license for ...

Belarc Advisor. Get it from http://www.belarc.com/free_download.html.

It tells you everything you need to know on your Windows systems, hardware and software, even including registration numbers.

It's free, and doesn't report anything back to anyone.
In other words, it's not spyware or adware.

Actually a pretty useful tool.
Not only tells you what you have on your system,
but reports free memory slots and current CPU speed as well.

Print the output, use as a handy reference.
Should you ever reformat, the list might come in handy.

You'll likely discover software you didn't know you had.