Shadowgate

I remember playing it at my father's work many years ago, and I'm pretty sure that computer had at least 7.1. I can't remember if there were any Help Balloons, but Taskmaker was on that computer.

I found this with Google:

http://www.euregio.net/english/computer/games/s/X0025_Shadowgate_solution.html

The answer seems to be yes.

On my PB 160 with 7.1, it loads to the startup screen, loads all of the windows, than shows a blank box and crashes. Deja Vu and Uninvited work fine on the same system.

Unfortunately, the standard version of Shadowgate is not System 7 compatible, but there was a hacked version floating around at some stage that supported some version of System 7.