1) If you ripped them yourself to mp3s, you're fine. That's exactly what you should do. *Everything* plays mp3s. The above rant is about the lockin you get from paid music downloads.

2) I'm not a Windows user. Trish uses iTunes. You need to fiddle slightly with preferences to make it rip to mp3 rather than the slightly less compatible aac format.

3) The shuffle does let you play in order, but you can't see what you're doing. People say good things about iPods.

Using the Apple products is fine, it's just the music store which really locks you in.