doubletwist will automatically sync your itunes with a Droid, but be careful if your itunes are all ALAC. I did this and it downcoverted all my songs to MP3 quality. I initially thought my Droid Bionic sounded bad, until I checked the card and saw it was only 2G full compared to the 9G of ALAC in my PC's iTunes. That was what caused me to find Poweramp. I can drag and drop either songs or whole albums from my PC itunes over to the phone and they stay in the higher quality ALA. I have not figured how to sync my itunes playlists or the entire library at once.
i also have a playlist issue. Everytime i connect my Droid Bionic to my PC and transfer a new ALAC file over from itunes, Poweramp does a search and all my songs in my playlists are gone. Playlists are still there, but i have to resave every song again to the specific playlists, which is very time consuming. Any recommendation on how to avoid this? thanks