I have the Nano and I recommend it. It stores songs on a flash drive rather than a hard drive, so it takes A LOT to get it to skip.
It really depends on what he wants it to do. Does he want video? Will he want to be able to set up individual playlists?
DH doesn't like the Apple products, because he has this thing against Apple. I really like the iPods and I buy all my music from iTunes. If you're going to use iTunes, the iPod is your best bet.
Outside of the iPod line, the Samsung Pebble is a nice choice as is the iRiver Clix.
You can go to
Tech product reviews for cell phones, computers, M and read reviews of different ones. They'll list specs and pros/cons of each.
