AFAIK as long as your DAW supports the VST format you want (ie 32 vs 64 bit, VST 1-2-3, etc) windows isn’t an issue. The issue is at some point you aren’t going to have new DAWs/updates support anything other than 64-bit VST3.
If it goes deeper than that (ie a plugin relies on some sort of library that was in old windows but not newer versions) then I haven’t encountered it. I don’t really want to use anything more than 10-15 years old, which goes back to Win7 times, which still seems to be the benchmark for “modern” windows.
On Win11 I’ll update when I next get a new PC, but I’m not eager to jump into it. Probably going to buy a new laptop for music when the new Intel/AMD laptop chips come out in a few weeks/months, so I think that will come with Win11.