Personally I can highly recommend the iPod. You hear more about iPods breaking than any other device simply because they vastly out-sell the other brands' devices.
I'd strongly recommend using
iTunes however to organise your music. It works especially well with an iPod, but it can organise your music for any player you choose, and lets you 'rip' your CDs (turn them into mp3 files), as well as 'burn' (create) new CDs with your favourite songs on. Just make sure you go into the preferences first and change the import settings from AAC to mp3 so that the files are compatible with all generic mp3 players.