I've had more time to play with the PSP now that I got a 1GB memory stick for it. I succesfully downloaded some episodes of Battlestar Galactica that I had missed and re-encoded them for my PSP. Most of the setup was painless, but there is a lot of waiting between steps. At least I have several episodes now so that should hold me for awhile.
I had a much worse time trying to get TiVo programs onto my PSP. It appears that either you're lucky and it works or you're unlucky and you have to add some extra time-consuming steps and software. I'm an unlucky one so I'll have to re-experiment with my other options to see how they work out. I'd rather it not take 10 minutes for me to load 45 minutes worth of programming to watch on the train; at that point I'll just go back to reading books.
I dream of the process as simple as iPod + iTunes, though we as consumers have much less control over our video as we do our music. If Sony were consumer-friendly, they would have released a program for the PSP that would let me transfer my DVDs onto it painlessly. Instead, they want me to pay $21 for a UMD version of Kill Bill even though the DVD version is only $15. Go figure. The only comparison that comes to mind would be if Apple had released the iPod and told it's customers that it would only play $20 albums from the iTunes Music Store.