I was thinking along the lines of an ipod shuffle - can get one for under £30 (which is half of what I have available to spend - bonus!) with my staff discount at work and they come in funky colours. Also love the built in clip so he can attach it to his clothes. Only downside is no screen so he can't just skip to 'track 4' or whatever, he'll have to flip through. Others around the same price but with screens seem a little complicated for him, I like the shuffle as it is simple.
Anyone got any other ideas or got a shuffle and know whether it would be suitable for him or not?