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It's a mix of luck, planned obsolescence, and parallel product compatibility evolutionary divergence. (that last one was a BS term cuz I don't know how else to describe it). In other words, product "A" worked with OS "B" before but for any number of unknown reasons, there's no guarantee it will with today's latest versions.
If by "Not approved my MS?" you mean "Not profitable for MS", yes that can be one interpretation. Goes without saying, every vendor wants you to buy their newest stuff.
Tried "XP Compatibility Mode" in Win 7? It works with some stuff not with others.
You may also want to look into OS emulators. Considering you'd like to run Win3.11 stuff in Win7(eons between), that would be the general direction I'd aim at exploring.
Myself, I like to keep a bunch of different machines with different OSs for whatever programs need to run on whatever OS. For my practices, that keeps it simpler and easier.
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