In general, it sounds like you're expressing frustration about support and application lifetimes. I work with a mac user and he experiences the same thing so it's not something that only affects the world of windows.
Just because something works now doesn't mean it will continue to - obviously the issue of support is an area that is important in the real world and keeps IT people busy. Applications become abandoned, even open source ones, and device support is dropped. The landfills are packed with devices that worked perfectly well but don't have drivers for a more modern OS.
Sometimes you do have to just move on, even if it's a PITA (or wallet).
Virtual machines are one way of extending the useful life of an app, if your machine has the horsepower to run one.