I use DoubleTwist and although it was a pain to get all set up on it because I had so much DRM music, I'm rolling along just fine now.
What I did:
1. Download a program to remove DRM. I used iSkySoft, but there are cheaper ones.
2. Use the program.
3. Now the fun part: go into iTunes and click "show duplicates" in the file menu. It will bring up your DRM songs and their now DRM-free versions. Remove all the DRM ones. This takes awhile if you have a lot of tunes purchased before mid-2009 when Apple had to stop that. Show the "modified date" on the columns to make sure you delete the right one!
4. And now even WORSE: rebuild all your playlists. Deleting the DRM file does not automatically replace it in playlists with the non-DRM file of the same name. Suuuucks.
5. Run DoubleTwist and sync.
6. PLAY.
I had hundreds of iTunes with DRM and it was a mess to do this, but it had to be done to get them to work on any non-iThing, so I just sucked it up and spent a few hours and now I'm good to go with DoubleTwist, iSyncr, or many other programs and devices.
It WORKS. It takes one big time committment at first, but it works. You'll have to do this no matter what non-iThing device you get.
Since most stuff on iTunes now is DRM free (so far as I know) I don't have to worry about my new music downloads.