Had a couple of sony players in the past and stuck with them for a while but the headphone sockets kept breaking after about a year. Great sound quality though.
For a while I had an iRiver (can't remember model) which was pretty good in some ways (easy to drag & drop files, good battery life) but was a let down in terms of sound quality and useability. The menu system was a pain in the nuts, and it refused point blank to play some albums in the correct order, no matter what I did with the file info.
I inherited an iPod nano and was going to sell it (I too had issues with the apple marketing bollox), but after using it a wee bit to see what the fuss was like I'm a convert. Sound quality still not as good as my sony players were, but the user interface really is superb. I even quite like iTunes.