The Sims is like an obsession. I have all the expansion packs for all three games. I find stuff packs to be a waste when I can download better content online. And don't even get me started on this store business.
The Sims 2 is the best out of all 3. I would put the Sims over Sims 3 as well, but that is only because for some reason I can't get hooked like I used to with the Sims 3. I still buy expansion packs when they come out, but I grow tired of it after two hours of gameplay and don't pick back up again until like weeks later. As compared to Sims 1 and 2 where I could play all day if I wanted. I guess its because I'm older.
One of my favorite parts of the game is actually creating the Sims so I didn't really play pre-mades like that. But I did enjoy the families in Pleasant View (Calientes and Lotharo>>>>>>>)in Sim 2. The Sims 1 families were cool. I didn't even bother with the pre made families in 3.
As far as expansion packs go...
Sims 1: Makin Magic, Superstar, Unleashed, Hotdate
Sims 2: Nightlife, Seasons, Freetime, University
Sims 3: Late Night and Ambitions
I can never get past generation 3 in any of my families so, yeah. Legacy challenges are no different.