I feel your pain. Since the last patch I haven't been able to sync any video podcasts...and I've done everything listed on the forums...rebooted, reformated, reinitialized, reinstalled...nothing works. Months, it seems like, since I've been able to get the zune to perform as it once did. I've not been able to get any support via the authorized channels. I think they are not supporting the Zune30, which is the one I have. Unfortunately, I puchased it without knowing it was being discontinued. I got it because it was big enough that I could find it in my bag. Heh. (Also because I'm a MS shareholder, and wanted to buy MS products.)
I'm thinking it wasn't one of my better purchases however. I primarily use it as a podcast transport and audio book player, rather than as a music player...and as much as I don't want to give money to the company that gave us institutionalized Ismug, I may have to go with an Apple product, because I've spent too many hours trying to get the Zune to work the way it did before the latest patch.
You would think that MS would be able to put out a product that could seamless download, sync and play things from the Marketplace. There's no excuse for stopping support of a product that is less than 5 years old, unless they were going to provide a significant discount to upgrade to a supported product. There's no excuse for a software update that removes functionality or turns 2 year old products into bricks.
The entire experience has left me less than pleased.