There's a GTA clone game comming out called Streets of L.A.
Saw it at E3 and it's nice. A little different than GTA in the fact that you are a cop with an attatude
I love my Xbox, wish I had more time for it. Definetly dont' regret getting it.
Live is about $39 for the headset and the one year subcription which is worth it. Don't have it yet but plan too.
PS2 looks very dated now imho.