I don't know any other free syncing tools, but i think The Missing Sync
is the most known and best with mac working tool...
Hi Andrew, the missing sync seems to be the best one but its $39.00, I have tried Double Twist (free) but found it did not like my Itunes it told me all my music was DRM protected, which it isn't. So I used Sailing Media Sync again free but a bit limited and slow but it imported all my itunes inc playlist. So guess you get what you pay for.