I have tried HTC Sync v.3 (can't remember where did I get it), anyway this version has complete different interface to version 2. In the music secion, it does has sync with iTunes playlist, but when I select it, it doesn't sync to my phone.
MacBook Air 13" (OS X 10.7)
iPhone 4 Black (iOS5)
HTC Desire S (2.3.5 with Sense 3.0)