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Make sure your router/firmware is on the list of approved LIVE routers.
http://www.xbox.com/en-US/support/co.../equipment.htm
The behaviour that you're describing sounds very much like you're behind a router that LIVE does not like. A quick way to test this is to connect your computer directly to the modem, and see if you get different behaviour.
Thanks, but I figured it out.
The culprit? Vista's crappy handling of my wireless router's signal. When running OS X on my iMac my signal reception is usually better than when running Vista... I don't know why... maybe it has to do with the Vista drivers Apple provides for its Airport Cards...
I also have a Macbook Pro, and that gets GREAT reception. For some reason it almost always gets better reception that the iMac even when they're right next to each other... maybe it's because of the metal case or something.
I tried using the vista anti-lag program. It didn't help. I also tried connecting my iMac directly to the router - it worked fine. It was also okay when I brought it downstairs near the router and let it connect wirelessly. So the wireless signal was the problem.
So here's what I did.... I just used the wireless signal from the macbook pro; I enabled internet sharing on the MBP, and connected it to the iMac (which I had running Vista) via an ethernet cable. I was basically using the MBP as a bridge.
It works great, and I think I deserve one hell of a cookie for coming up with that solution :D.
Thanks all for your help and suggestions though.