The setup I use is an IPod Shuffle, inside a waterproof case from
Otterbox, and earphones from "Waterproofmusic.com or .net." There's a
few other things I've tried--waterproof players from Swimman and
Freestyle Audio--but this was the most flexible and economical set-up
for me. Now, I stick the Shuffle in a rear pocket of my shorts and
have the wire going up my back, which causes suprisingly few problems,
even using all strokes. Earphones stay in by using over-the-ear swim
cap (Aqua Sphere Silicon).
All this works pretty well, except the earphones are not ideal. If
you've ever tried anything like this, you'll be familiar with the
trouble in getting them to fit just right so that water doesn't get in
and block the sound. But.. I've approach.a few companies about this
and they all claim to be coming out with much improved earphones in the
next month or two that will solve the problems (and, I assume, they'll
all sell them separately from their own players). Companies are
Swimman, Freestyle Audio, and h2o Audio (which looks like it currently
has a nice set of earphones, but doesn't yet sell them separately).
Hope that's helpful,
Jon
P.s., note, if I was a more serious swimmer, and price was no object, I
would probably opt for swimman's setup, as their player is so small,
you can clip it to the back of your goggle strap.