I seem to remember a Cassidy & Greene program that would do all sorts of statistics to your extensions. I mainly used it to do a binary search to figure out which extension is causing the shareware app of the day to crash.
Conflict Catcher! By Jeff Robbin, who later wrote SoundJam MP, which was then bought by Apple and turned into iTunes, and he stayed at Apple for many years (may still be there even(
This was one of the only games I actually played in the Macs they had at elementary school (we spent most of our recess time on Napster...playing 12 different songs simultaneously in the same room, and nobody cared). I spent so long looking for this game, but I couldn't even figure it what to search for, because I didn't remember the title.