Hi,
I using an iPod Mini for several months now and can give you at least some first answers (but if you need other information or have more specific questions feel free to ask here or contact me directly...):
1. What challenges would I have? (if any)
- barely any. iPods for once are truely self-explaining and easy to operate, even if you would pare them with a Windows PC (as I do). But note: the only really comfortable way to operate them is with iTunes being installed on your PC, which has one important disadvantage: in the standard setting it automatically synchronizes the iPod with the music library on the PC, which means, that if you connect the iPod first to your PC with all the music and then later to another PC with no music on it, it will delete everything on the iPod as it synchronizes with the empty library. For technical questions like this and some great tips, e.g. how to set up playlists that shuffle through all your music even if not everything fits on the iPod take a look at
http://www.ipodlounge.com which I found to be a great source, especially the forums.
2. Would I have issues with compatabilty issues using Tokyo copy protected CD's?
Never tried those so far ... I'll do in the next day and will update you if noone else posts. I do have experience though with the copy protected CDs from Sony, BGM etc. sold in Europe and those never created a problem with the exception of two CDs, one I was unable to play in iTunes at all (so I made the MP3s with a different software and imported them into iTunes) and another one where the last track did not play in iTunes (same trick as before worked perfect once again).
3. Are all the track listing available in their library? What about Japanese releases?
Not much of the Disney theme park releases are available in the library, which by the way is not iPod / iTunes specific but one of the general libraries (forgot the name and don't have iTunes installed on this PC, so can't take a short look - sorry). Those that are available often are far form perfect or contain numerous errors, so need to be corrected by hand in iTunes.
Hope this made the start easier...
Yours
Dirk