Ofcourse, songs you buy from the iTunes store are protected and will only play on iPods (i personally don't buy songs from iTunes anyway). I simply create a playlist in iTunes, run SyncTunes and it transfers it to my Samsung device. It lets you sync your iTunes playlists to any storage device. Now, as to syncing with iTunes, you have a few choices. It's mass storage, so it shows up as a drive and you just drag and drop.
I currently have a 1GB Samsung YP-MT6Z, absolutely fantastic, with SRS WOW sound effects built-in. Most of them are Mass Storage compliant (drag and drop, no need for proprietary software) and have FM radio/recorder, Line-in mp3 recording and voice recording and run for 42+ hours on one AA battery (YP-MT6Z). I have always preferred Samsung YEPP mp3 players.
IPods are not for everyone and they do lack some features that others like myself prefer a lot.
