Really nothing to worry about SirN. All of the software you've mentioned is no longer supported by MS, so you wouldn't expect anyone to come looking. There have been plenty of academic versions up for sale by individual sellers, as well as promotional samples and items not for individual resale that get sold every day. Owning the packaging and software is also quite different to installing and using it, but unless you are intending to generate serious income with legacy products, there would be little cause for concern over a breach of license conditions.

If you didn't buy education/academic software back in the day, well it was basically just the retail version but with the proviso that you couldn't use it for anything other than a teaching/learning/research purpose. As a student for an extended period (undergrad/postgrad) I was able to buy loads of software during the Win2000/XP era for home use on this basis, even if sometimes I didn't meet the course load requirements for the academic license i.e. full time hours. The need for a student ID, or in some cases a university or college email address, only arose at the point of sale, but activation was done using the same methods as for retail software - and during activation via telephone they never asked for my student ID information.

In respect of the contents, there were some packages that were full retail but with an academic version sticker on the box - one such package being Visual C++ 6; I needed to show student ID to buy it, but there were no other obvious markings on the contents. I have a version of NT 3.5 which has the same sticker. Other software, such as Visual Studio .Net Academic (2003), was quite different, with all contents printed to show that it is the Academic version. I'm also a collector of old software, but try to avoid academic versions as the additional markings or stickers does make them stand out a bit compared to full retail!

Not really planning on turning a profit with any of it. 😀 But, I do some coding in Linux and embedded stuff, and want to learn more about Windows development. Some of that could eventually make its way to niche groups of users. I don't want to get flogged for compiling a Win9x version of a library with an academic copy of VC++. Even if I track down a supposedly retail copy, disc-only, to shore up an inappropriately-licensed shelved boxed copy, I'm not sure I would be able to tell the difference if it's merely a different key or something. I've heard some copies have an expiration (but also that that's not actually the case) and all kinds of other things. No idea what's really true, and most of the documentation I've found is more like what you're allowed to do, not what you can do.

I'd argue messing around with old software is academic use, unless of course you are supporting legacy software. Most of us that do more then just retro gaming are using software to educate ourselves who things were done in the past.
Not saying it would stand up in court but should help you sleep better at night at least.

Re crippled software, It would be on a application basis and even if it is if the missing feature may not even be needed. Say something like cluster fallover on SQL was removed, Meh wouldnt use it anyway