Well I got a Zen for my last Mp3 player, and it was difficult as hell to load MP3s on, and the headphone socket eventually stopped working.
So I got an iPod Nano and have had 0 problems with it (it's not very old yet though.) It's interface rules and iTunes makes loading so simple. If you're going to get a Nano, make sure you get a case to go with it though as I can't stress this enough, it scratches mindbogglingly easily. It hasn't come in contact with anything except the box and my hand and it's already covered in micro scratches.

__________________


Command your people; climb the mountains
Their peaks shall become the shore
The darkness will be defeated
But Hyrule will be no more