The Windows version (a legal, non-cracked, copy, even) runs well in QEMU. Pretty sure I managed to get it working in WINE as well at some point, but I prefer to have software running in QEMU as that tend to be much more install-and-forget rather than having to fiddle with settings or/and reinstall stuff every time there is an upgrade or I move to new hardware.

OG iMac for the retro coolth of the project, or for ease of installation?

Because the Windows version works perfectly under Wine.