I'd been using iSyncr for a while with iTunes, but to be honest, I wasn't actually buying too much music on iTunes since it had a brain fart and wiped out $150 worth of my music.
But I recently set up a PC with Windows 7 Professional and iTunes was one of the applications my daughter uses a fair bit to sort out music and playlists for his iPod.....and I got back into it.
OK, so I bought some songs. Time to check out how to best handle them with my Samsung Galaxy S Android phone.
I bought the iSyncr Wifi Add-on (US$1 / NZ$1.22). It works with iSyncr 'regular' except you don't need a USB cable to sync. You do need a Windows or Mac PC for the PC 'server' of the iSyncr app to run on. (I have not tried it in WINE on Linux...mainly because I don't run iTunes on Linux - yet).
The app let me choose the categories I wanted to sync (music, movies, photos...etc) and then it just syncs them. Playlists, too. DRM-protected movies do not sync. Music comes across fine as mp4 files as usual if you use iSyncr. That's what I was mainly interested in and it works great.
If you have any use for iSyncr then I recommend this add-on. Getting rid of the USB cable is just that wee bit better.