Get an MD player/recorder with NetMD/Hi-MD.
I've honestly never gotten my MD player to skip, and extra storage is super-cheap.
I also cannot stand players that randomly select tracks from a big playlist. It's a pain navigating through 20gb of music with the limited controls on those things.
Besides, in terms of looks, MD players far out-pimpify anything out there. Go for a snazzy Japan-market only one from
http://www.minidisco.com
Only thing is, MD sound quality is GOOD if you are using serious earphones. For this reason, MP3s encoded at a lower bitrate won't sound very good. I use Grado SR-80 headphones, and they are pretty unforgiving of bad recordings.