If you want something older than Windows 8, Windows 7 is very good and it's still supported by Microsoft. I play JKA with the .ISO files and use UU to run it, all works fine on Windows 7. Except for older games like Republic Commando and Starcraft 1 (sadly I can't run them on Windows 7).
a friend of mine was having trouble loading the game via windows 10. i mean just the game in base form (1,0). Tried updating to 1.01 and still didn't help.
does he need to run compatibility mode for jka also? btw im a steam user and don't have any issues with mods,skins, or utilities. I have a gamedata folder just like yall do