So I've trying out wi-fi syncing with Winamp and doubleTwist, and so far the experience has been less than satisfactory. On Winamp, I got it to recognize the phone, but it promptly dropped and I haven't been able to get it connected since. Trying to get support for it has been next to impossible, as they haven't replied to my message yet (it's been weeks) and nothing in the forums has fixed it.
I tried doubleTwist with AirSync, and the desktop version found the phone just fine, and I was able to AirSync most of my library to the phone. However, I had to interrupt it as I had to leave (it had been going for over two hours, and I have 8GB of music), and when I came back, it was unable to connect to the phone ("Network Error"). I had to restart both machines, but it then either didn't recognize the phone on the network, or gave a "Sync Failed" error. So far nothing I've tried has been able to re-sync the phone.
My experience with wi-fi syncing on Android has not been good, and since iTunes is superior to both apps for music and podcasting, I am going to buy the Verizon iPhone and see if I get a superior experience. I really don't want to be subject to Apple's restrictions, but the less-than-satisfactory media experience on Android has really turned me off to it being a media device.