Because Apple won't unclench

I have an iPod Touch. Quite useful, definitely like the ability to listen to podcasts at 2x speed. Wish the normal music tracks had that feature. And the feature of skipping back 30seconds. (Because by 'music tracks' I generally mean other podcasts/rpg game sessions that I don't download via iTunes.)

And iOS v5.0.1 is out. While I don't necessarily need to, I could update my iPod to that. Just to make sure everything is running at top efficiency...

The problem is is that when I got the iPod, it came with movie files on it. (YES, legally. It was part of a thing this website was doing.) But, iTunes doesn't want to have anything to do with them. If I tell iTunes to 'sync', it wants to delete any files on the iPod to load on ones it does know about.

And... of course... and this is the problem, it's not like any other software is letting me easily access the iPod. (At least none that look to be free that I would trust.)

But, and this is the kicker, if I want to update to the latest iOS, it warns me that all apps and media will be deleted. (It doesn't acknowledge that the computer I'm connected to is the one that I sync with, so it can't backup the files on the device.) I don't want to delete the files. I don't have copies anywhere else. So... I can't update the device.

Really, Apple? Is it so hard to let other people manage files that go off or on the device? Am I forced to consider jailbreaking the thing just to back up my perfectly legal files?

Does anyone else out there know what the solution is? Is there free software that can copy all the files off? Or is there some setting I'm missing that stops iTunes from deleting everything I haven't given money to Apple for...

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