9/2007 UPDATE: The steps below should still work fine, but now there’s an easier way: try iPodifier for Windows. It’s free! I haven’t tried it, so if you have problems, leave a comment. There’s more information on this whole process at Lifehacker as well. Vista MCE to iPod may or may not be a problem, but is anyone really using Vista?

Steps
1. Download and install iTunes 6 for PC.

2. Download and install DVRMSToolbox. Media Center files are recorded in a format called DVRms, which I think is MPEG2 with an xml wrapper. DVRMSToolbox allows you to convert DVRms to more accessible formats. You have to install the latest .NET framework (shiver) if you don’t have it. I went with .NET 1.1 instead of 2.0 beta.

3. Run DVRMStoMPEGGUI. You can convert a whole directory full of files or a single file. Let’s do the single file.

• Double click on the “Input File” field and select a TV show from your drive:\Documents and Settings\All Users\Documents\Recorded TV folder that you want to convert.
• Double click on the “Output File” field and choose a save directory and a name for your file - I’m converting an Aqua Teen Hunger Force episode, so I name it “aqua” and save it in my “My Videos” directory.
• Choose the “Convert DVR-MS to MPEG w/o commercials” profile.
• Everything should look like so:

4. Hit run and go get a Coke Zero. The fifteen minute Aqua Teen episode took about five minutes to process on my Semperon 2600+. Not bad.

5. Now that you have a generic MPEG file without commercials, you need to process it into an MPEG4 video file the iPod will take. If you want to stay on the PC side, pay to unlock QuickTime Pro, follow Apple’s instructions, and sync the video to your iPod. If you want to do it for free, take the MPEG2 video from DVRMSToolkit to your Mac and process it with FFMpegX, following Mark Pilgrim’s tutorial. I thought for sure that PSP Video 9, a free Windows program, would work, but I tried a bunch of different settings and couldn’t make it happen. Please leave a comment if you know of another free Windows tool that would do the job.

6. Annnnnyway, at the end of all this, you are here:

You’ll notice the clip is only 33 seconds long; I encoded just a clip so I could get the screenshot quickly!

Sync your iPod and congratulations: you’re a pimp. With luck these instructions will be swiftly obsoleted by some clever soul who writes a drag-and-drop app for converting DVRms files to iPod-ok MPEG4 or, even better, a one-button sync plug-in for MCE.

Look, it works! Yeah, it’s a bad photo.