I've noticed timsamoff and Totololo saying they use iTunes. I'm totally unfamiliar, and not inclined to learn much about it.

But I'm thinking of buying an MP3 player for a teenage son of a friend. He's had two iPods stolen, and I'm not into spending the big Apple bucks. Since all his music is in iTunes (on a Windows PC), is it going to be a big pain for him to get it into a non-iPod, like this good-looking deal on the Dane-Elec Meizu? He isn't a computer idiot, but he isn't a geek and he's not a patient person either. Is there some program that makes it simple? I'm willing to learn some to help him, but I'm not that big a music buff and I've never even made playlists. (I'm happy with Vagalume and CDs or whole ripped CD's.)

Here's a sample of what worries me, and a response. (That response is not heartening enough, btw.)

I know this is way off-topic; but that's why it's in the off-topic category.