I've very much enjoyed playing SimTower, and I still have a legitimate exe of it sitting around. But the game is a Win16 game, and my latest experience running it in WINE was crap (it became very easy to completely lock up X). Possibly it might make more sense running in Windows 3.1 in dosbox.

Incidentally, this is a motivation for why I'm playing a bit with statically recompiling x86-16 code to run on x86-32.