SETUP
    If you have an iPod, you can go onto iTunes and manually purchase TV shows to watch on the go for $1.99 each. Or you can subscribe to a TV show for $40 and get them automatically.  Well, with Windows Mobile, you can get ANY TV show automatically synced to your device as soon as it has been recorded off of your home digital video recorder for free.  As long as you use Windows Media Center, that is.  But guess what... if you've got Windows Vista Home Premium or Ultimate on your computer, you're almost already there.  All you need is a Windows Media Center compatible TV Tuner.  You can find these TV tuner kits for around $100 and many of them just plug into the USB port on your computer.  Plug the TV tuner into your cable box or antenna and you're ready to record your favorite TV shows for free, even if they're not available on iTunes and without paying a monthly fee for TiVo.  Visit Microsoft's website more information about adding a TV Tuner to Windows Vista.   

In Windows Vista Media Center, go to Tasks>Sync to set up syncing with your Windows Mobile Device. Be sure you've got a good sized memory card installed and select it when prompted.

    A selection of content is automatically created.  I suggest customizing this a bit further.  You'll have more options if you set up the syncing in Windows Media Player, however, Windows Media Player will not recognize the TV show series that you've subscribed to in Media Center unless you go to the Tasks>Sync section there first.  Also, it's important to note that if your Windows Vista Media Center system has been upgraded to the TV Pack which uses WTV files for Recorded TV shows... then syncing with Windows Mobile is likely broken.  A workaround for this problem can be found here.

    Instead, let's go to Windows Media Player and set up an automatic sync there using the Sync tab.  As you can see above, I've selected only the playlists I want to sync on my device. By default, Media Center generates "Last 3 episodes" automatic playlists of all of your Recorded TV shows.  You can find these in the "Sync Playlists" option under the Available Playlists pop up in the above Sync Setup dialog.  But what if you only want to sync the latest one episode of a specific TV show? 

Click the "New Auto Playlist" button, and you're presented with the dialog box above.  You can change the criteria for your auto playlist to almost anything.  I'll set mine for TV shows in my library whose Series name contains "Heroes".

Next you'll want to add a criteria that sorts the list of Heroes episodes by the date recorded in descending order. That way you'll always get the newest episodes. 

Then in the Restrictions section, I'll limit the number of items to 1.  This will create an auto playlist that always consists of the latest 1 episode of Heroes.

Next, make sure that new auto-playlist is added to your device's sync set up. 

    From now on, the newest episode of that TV show will be synced to your device whenever it is plugged into the USB port!  You might want to leave it plugged in overnight, since Windows Media Player will automatically convert the recorded TV shows into a format appropriate for your device.  With Windows Mobile Devices, that means WMV format, and it can take a while if you've got a lot of TV shows to sync.

When the syncing is finished, open up Windows Media Player on your device and navigate to the "My TV" section of your library.  You'll see you've got your favorite TV shows ready to watch where ever you are.

CONCLUSION

For more useful tips and tricks, check out The Touch Diamond/Pro Tips and Tricks Guide.