iPad VGA output for the iPod app?
I would just look in the app store for a video playback app that supports VGA output. Lots of them do now.

You don't need to jailbreak your phone.

Here is an app called "StreamToMe" that supports playback of your videos over 3G and Wi-Fi and has VGA output.

StreamToMe: http://itunes.apple.com/us/app/streamtome/id325327899?mt=8#