I find myself not playing TS2 as much anymore. :|

[Late Shift]

You could always try the Apocalypse challenge. It is made by the same guy who did the Legacy challenge... It is fun, but has a mass of rules to understand to start with. Very challenging, and very hard.  

[`R a i n b o w]

The rules of the legacy challenge is basically what bothers me. Idunno why, it doesn't sound appealing to me. I think I saw taht challenge somewhere and I don't think it did either.
I've onyl married an NPC once, 'cuz the genie picked her as my blind date once. 'sept..no.. Ididn't marry her. I WooHood with her. And I never talked to her again. She was the pizza lady. neutral

Anyway, most challenges don't seem too sppealing to me, because the the strict ruling. And I don't like the fact that I'd have to keep track of points and stuff [though, I don't have to keep track, really]
Idunno.

 

[Lady Vina]

In Armatage's link to the list of challenges, I thought the barista one was interesting. I'd been playing the Sims 2 less but since I found that challenge I can't pry myself away from it.  

[Infinity-Nevermore]

Some of these challenges look interesting, but I currently don't have time to play. But believe that when I get off for Christmas break I will return to TS2.