Go with an iPod, they have the best User Interface, and are worth every penny. My two suggestions would be the new
iPod Shuffle, which will be out in a couple weeks. It doesn’t have a screen, but is super tiny, and super rugged. It is 1 Gigabyte, which is approx. 240 songs. If you think he needs a screen to see what song is playing, or other stuff like that, then go with the new
iPod Nano. The base model is 2 GB. It is very thin, thinner than a #2 Pencil.
As for free mp3 downloads, you can find some bands that offer there music for free on their websites, but these are usually new bands, and you won’t find popular songs for free legal download.
Do you have a large collection of CDs? If so, you can take the songs off of those, and make them mp3s very easily. Other than that, I would suggest using the iTunes Music Store. If you get an iPod, it will come with the iTunes software, then it is very easy to buy songs for 99 cents apiece.
I hope this helps.
Feel free to email me if you would like me to go anymore in depth on any thing I said.
Yours in Christ,
Thursday