Tivo ToGo for PSP and iPod Video
I'm not a huge fan of paying for media conversion software that's technically already available for free in other variants, but if it makes my life easier, $25 is a small price to pay. Tivo Desktop already connects you up with any of the many Windows Media compatible devices to watch Tivo recorded shows on the go. They've recently added the Tivo Desktop Plus, which now supports output for both iPod and PSP hardware, as well as Treo and Nokia cell phones. This gets you support for converting all Tivo ToGo shows in a format compatible for your devices without the configuration hassle associated with some of the free alternatives. Output formats are available as either MPEG-4 or H.264.