New user, just got my Milestone, moving from an iPhone 3G as I was sick of the stereo bluetooth that hardly ever worked properly and lack of AVRCP. Now don't get me wrong, iTunes is a bloated mess, but the way it does podcast sync and that integration with the iPhone is hard to beat. What are your setups to get close to that on the Droid? Currently I am using DoubleTwist to download and sync podcasts to the phone, which works pretty well. I tried bTunes as a player which was nice but it doesn't work with AVRCP (bluetooth headphone controls), so I am using MortPlayer which does work. Of course as the Droid doesnt have a database of the music like on the iPhone there's no way for the sync app to know whether you've listened to the show or not. Are you manually deleting the shows on the device after you've listened to them?