Sync issues w/ music and video

I'm a proud new owner of a 16GB iPod Touch and absolutely love it. However I have been running into some issues when transferring files from iTunes to the Touch. Transferring Videos or music from iTunes to the ipod appears to work. It shows that they are sync'ed and a transfer is in process. The file (video/audio) shows up on my ipod. But this is where the problem arises, and it's random. I'll play a video on my iPod Touch, and at any point in the video it will just stop playing and go back to the video playlist, like the transfer was incomplete. The same will occur for music. It will show the song/video, the proper length/time of the music/video, but at certain points the song/video cuts out and goes back to the playlist, as if the transfer was cut. I've tried more than 2 iPod cables and all the USB ports on my PC to no avail. If I delete the file, and re-transfer it in iTunes, there's a chance the transfer will complete so it seems like the sync corruption occurs sporratically. Is there any insight as to why this occurs and a possible fix??
Using iTunes 7.4.3 w/ iPod Touch 1.1.1 firmware

I have an Alpine receiver with Parrot bluetooth in my Jeep. Got a new iPhone 3gs with ios4. every time I start the Jeep, I have to enter the BT password and reconnect to the radio from my iPhone. I had a basic Motorola and basic LG phone that automatically synced with the radio every time I turned on the Jeep as long as bluetooth was active on the phone. Also had a Droid X that also auto synced. Just had to pair and connect with the pw the first time I used it. I don't know if this is ios4 related because I didn't have the iphone before.

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