I have two semi-related issues and potential fixes.
1. I have issues booting up when my external monitor's USB hub is plugged into the Macbook Pro. There is an external harddrive attached, which may be the root of the issue. Around 50% of the time it freezes on the boot disk selection screen.
When the boot hangs, I unplug the USB hub, turn the power off/on, and hold alt to bring up the boot selection menu. I've never had an issue booting into Windows when I unplug my USB hub with the external harddrive.
I'm not sure if this update fixed my issue, need to check my EFI:
http://support.apple.com/kb/TS3423
2. My computer will freeze randomly in Windows 7 (64bit). I believe the issue is related to the graphics drivers on my GeForce 330m card. There are two options, so far the first one has worked for me.
a. Turn off Aero graphics. Goto: Control Panel\All Control Panel Items\Performance Information and Tools and then on the left click on "Adjust Visual Effects" Select the "Adjust for best Performance" to unselect all options.
b. Update your video drivers to something other than the default Bootcamp video drivers. (Start looking here:
http://wilby.com/cameron_blog/?p=118)