Question: MP3 player management software (a la iTunes) for old people

[theholycow]

I have two old guys who want to use mp3 players to play books on tape. I'm faced with two challenges:
1. Finding an mp3 player with fat-finger buttons and large-text display
2. Finding mp3 library management software that can be used by old people

How would I find such software? It needs to be simple, consistent, and automated. I can't have them buy an mp3 from amazon.com, download it, and then have to find it so it can be imported (besides the extra steps involved, it's asking too much for people to find where they downloaded their files to). It has to get found automatically.

iTunes is out because AFAIK there's no iPod for old people (and because I hate iTunes, let's not forget that). Maybe Windows Media Player? Would it be easy for old people to understand and use? Does it detect new songs automatically?