Swallow your pride, suck down the Kool-Aid and buy an iPod just like I did a year and a half ago. Get the one with the biggest hard drive you can. Just like gun safes, you will fill it up.
I have a 60GB iPod Photo. I love it. I seem to have an obsessive compulsion to try to fill it up, but I can't seem to do it. I currently have a month and a half of non-stop, non-repetitive, hi bit-rate music to listen to in genres ranging from Benny Goodman, to Miles Davis, to Frank, to Iron Maiden, to Dwight Yoakam, to ABBA, to Steve Roach, to Johnny Cash, to Elvis, to Leo Kottke (how can you not love Vaseline Machine Gun no matter how much of a Pinko Kottke is...and he is GREAT in concert) to Rush, to Trent Reznor, to a bunch of Feakish Shit that I forgot why I have it.
PLUS! A shitload of pics on it ranging from hi-res family photos to pics which if my mother saw, would demand I seek therapy.
I am only a tad bit over half full.
Come on in. Get an iPod. The water is fine.