I remember trying to play Phantasmagoria and it would have load of compatibility problems. Even sim city 4 I had to download a mod so it would run wide screen. Pc as this timeless platform, also struggles with dealing of older games ?

Actually I just tried to run jet set willy 2 again, this time on windows 8.1

"The program cannot start due to incompatibility with 64-bit versions of windows. Please contact the software vendor for a 64 bit compatible version"

Ok, so I tried DOS box that's supposed to run every old Dos game.
Setup runs fine, soundblaster 16 emulation works, yet trying the game
"DIV execution error: No hay memoria suficiente para ejucutar el juego. (load_fpg)"

Guess I still need my windows 7 PC if I want to run that game again.

Most Windows games of the last 15 years run fine. A few don't run on 64-bit-systems but most will. Windows 10 doesn't support some old disc protections like SECUROM, so these games need a crack or you buy the digital version (Steam, GOG) for a few bucks.

Almost all MS-DOS-games (1980 - 1997) run fine with DOS-Box, many of the best games from 1980 - 2000 (point&click adventures) run even better with ScummVM.

Most games with Windows95/98-focus (1995 - 2000) will be problematic, especially on 64-bit-systems. But GOG.com has already fixed many of them.

Dosbox, use it.