Ripping Music and Other Videos for new iPod

I have been having troubles updating the firmware on two older versions of iPod and as much as I hate to buy ANOTHER one - maybe everthing would be much easier.

Has anyone tried ripping video clips, home movies, concert dvds etc and had some success downloading them to the new iPod?

I also use iTunes but dont want to be restricted to their terms and content.

Thanks for any ideas using the new iPod.