Just get a 4th or 5th gen iPod and put Rockbox on it. They're cheap, easy to work on and fix if they break, and fairly abundant on ebay. Also, with Rockbox, you can just drag and drop your music onto it (like a regular USB mass storage device) and you may never have to use iTunes with it. I got a 60GB iPod Photo off ebay for a little over $30. All it needed to fix it was a couple good smacks (hard drive was stuck), and it's been almost flawless since then.