I must put in my vote for the iPod. We have had three different kinds of MP3 players and the iPod is the only one we haven't had trouble with. Yes, they tend to be slightly more expensive, but when you consider the cost of ownership, replacing or repairing, it is actually cheaper.
Also: iTunes is the easiest online music store to use and I think offers more choices for organizing our 4,000 plus songs into usable lists. Plus we