1. Braid is my personal game of the year so far, but it sounds like Geometry Wars is more to your liking, so it's tough to suggest one or the other. For what it's worth I never really paid attention to the leaderboards on Geometry Wars, as it seemed like most of my motivation was coming from topping my own previous high score.
2. I'm not a big shooter guy, so I can't really say. But I'd probably go with Halo just because of the online community (if you do go Gold) and the fact that I, too, am sick of WWII shooters.
3. If you like the Final Fantasy games (pre-XII), I'd really recommend Lost Odyssey. It's very traditional, which may or may not be a good thing to you. But the memory sequences are really beautiful and... well, memorable. 
Also, you should consider Fable II or starcraft will cut off your ears!
4. I'm not a huge online player myself, but for what amounts to a few bucks a month I find Gold to be generally worth it if for no other reason than getting early access to demos. Not sure about free weekends, sorry. 
5. Congrats on your purchase!
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