The iPod touch. 64GB should be plenty for your current library including several movies. My current library is at 15000+ songs, taking up little less than 90GiB, so you should be able to fit yours in 40GiB, since you want to rip at 256kbps AAC. And the touch is future proof, while the classic is not.
And this even comes from a person who has a soft spot for the classic..