Whereas my library of virtual assets will probably evaporate into ether before I'm even retired.
I would love that you be right. And by far, I strongly prefer physical media.
However, physical media is no guarantee either.
- Sometimes, the pain is on purpose: some apps require an online activation, and the corresponding service, 30 years later, is not available anymore.
- Sometimes, it's a lack of foresight from the developers (i.e overzealous Windows version checks, refusing newer versions).
- Sometimes, it's plain dumb stupidity (the installer is a 16-bit windows executable).
If you're not convinced, I suggest you try installing, say, Wipeout XL (for Windows 95) on a recent laptop (spoiler: at this point it's easier to play the PSX version on an emulator).
How hard is it to set up windows 95 in a vm, basically an emulator?