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use handbrake to convert the files (if they aren't already in the correct format), drag them into iTunes, sync your iPhone/iPod and on the Movies tab at the top, choose the ones you want to sync
I've not had a proper play with the latest update, but it looks like you can load all your films onto a server (your own) and then download what you want when you want it, so you could keep 100's of films on your own 'cloud' and just delete them from the iPad when your done.