Thank you for all the replies. I had started this thread to gather some options. I'm attempting Media Monkey right now. Can someone explain an easy way to .2s3ync my n900 with media monkey?
I'm still searching for a good, non-iTunes option on osx. Ideally, Amarok would work as well as it does on my linux boxes, but it doesn't. VLC is great for playing files, but I would like better library management. Any suggestions?