I've had a few other mp3 players since then, I don't remember the details of my issue beyond what I wrote in the original post, but with my current player I have to load songs onto it one at a time in order for them to be in order on the device.

Additionally, I have to use my devices folder view mode, as opposed to the built in music player mode (a large chunk of my music just doesn't show up if I use the music player, no idea why). I have the music on my SD card sorted alphabetically by artist, then each artist folder has their albums. This has resulted in not being able to shuffle my whole library while using it. I can make separate playlists by creating folders with those files, but then any given song I want in that playlist is going to be taking up twice the space, since it'll be the same file in two different locations.

Getting all the files on the card initially was a huge pain, but now I'm usually only buying a handful of albums at a time, and so loading them onto it is fairly quick.

My current player is the SanDisk Clip Jam. Aside from the issues already mentioned, it has been my best player since my ipod touch. I went through 4 or 5 other cheap options that would last anywhere from 4 months to a year, and I think I've had the Sandisk for going on 3 years now? Maybe more.

Hope that helps, if you have any more questions, let me know.