Ok, this is cool. Really, really cool. Long story short: I can automatically synchronize TV shows recorded on my Media Center box to my Windows Mobile smartphone. Read on.
Friday I picked up a T-Mobile Dash. If you're not familiar with this device, it is the Windows Mobile device to have right now. It's slim, sleek, usable and downright sexy to hold in your hand.
The first thing I did was hack the registry to restore the JOGGR functionality that T-Mo deprecated. Then I plugged it into my PC and synced up an album through Media Player 11. It worked as expected, copied album art and everything. Cool.
Then I tried syncing up a TV show I had recorded. It worked, except the resolution of the transcoded file was 160x120, which dumbfounded me because the device has a 320x240 display. After some searching, I finally found a newsgroup post linking to this answer. In summary, the device reports is capabilities to Media Center through a protocol called MTP. These capabilities are stored on the device in an easily-edited XML document (\Windows\WMSyncCaps.xml). Once I changed that, deleted and recreated the partnership in Media Player, everything started working great. The right resolution, good bitrate. Bonita! A half-hour show ends up being about 30 MB.
Back in Media Player, I created an auto playlist that holds the two most recent episodes of The Daily Show. When I plug in my Dash, the file gets transcoded and transferred to the phone's media library. (I have a 1GB micro-SD card, which might not suffice now that I see how capable of a media player this is.)
If I continue doing this, I'll plug my phone in at night, it will sync that night's Daily Show automatically while I sleep. Then on the train ride to the office, I'll be able to (have the option to) watch last night's Daily Show on my commute. How cool is that? Now I just need to pick up the headphone adapter...but it's out of stock right now.