First off all that ripping you have been doing......you get to do it again into MP3, WMA or AAC(iPod) for the players to recogize it. I do not know of any brand that uses FLAC. If you haven't been turned off by this, then you have to decide how much of your library you want with you at all times, if you can get by with 500-1000 songs then the 4-8gb sizes will work if you want most of your songs then you will need the 80gb or larger, beyond that you are looking at fancy new displays and some new features, etc.