Forget the i-pod, get a zenstone. It's $40 or so. holds 2 GB of mp3 files,
has an internal speaker, and rocks on headphones. Charges off the USB port,
and the software is accessible. Found it at Wolmart. Make sure you don't
get a fancy one with a screen.
If it's i-pod functionality you want, you can't go wrong. Spend $300 if you
want the exclusively blind features like speech synthessis.