Tried the first version of the sims, but it was way too tedious. You'd barely have time in the day to do anything since you had to manage everything.

That's just your OCD, I know people who would just get their sims to a decent level and then leave the game running over night to see what would happen. Sometimes they'd still have their jobs, sometimes the place would be spotless, other times the sim would be dead.

I've done it a couple times on my old iMac G3, but when I'd try to reactivate the game it would crash, not sure why.

I still have it installed on my G4 tower, been meaning to boot it up again, it was my favourite version of the game because your sims didn't age. Couldn't stand the idea that your sim could only live for 30-60 odd days.