[jigwashere]

I haven't tried WMP to sync. If it works, I'm all for it!

I've been using Handbrake to convert most of my videos. I picked the preset for iPhone, then increased the resolution width to 640.

My PC is Windows XP MCE. I record TV shows over the air and use MCEBuddy to automatically convert them, also using the iPhone preset. The advantage to MCEBuddy in this case is that it also removes the commercials. I happen to have an addon from Dragon Global (ShowAnalyzer) to remove the commercials, but MCEBuddy has that feature built in, too.