I tried to get some JumpStart games to run with DOSBOX a few years ago on Windows 7. Iirc I managed to install but not run the game.
I recently tried a bit to try and get another 16bit game run on Arch Linux with WINE in win98 or 95 mode but that still didn’t pan out.
Honestly it’s probably doable in some way without one but next time I try I’ll probably use a VM (Virtual Machine).
TIL
I didn’t have it set to true but I also never noticed any problem