problem one: it's way too slow
So folks are all a-twitter with the announcement that Tivo to Go will allow you to push your shows to your video iPod. Whee. But my GOD, has anyone actually used Tivo to Go? Or, more to the point, is anyone actually using it on a regular basis? May Wong of the Associated Press nails the TTG problem on the head...
Don't expect instant gratification: The transfer process from a TiVo Series2 set-top-box to a PC — a necessary step before syncing to a portable — occurs roughly in real-time. An hour-long show will take an hour to transfer to the PC, then roughly another 10 minutes or so to sync to a portable device.
So, it takes more time to transfer a show to your portable device than it does to actually watch the show. You can thank a crippled USB (1.0?) port on the Tivo device for this. I'm sure wily Tivo hackers have figured a way around this problem, but for your average person who just Wants Things to Work, this doesn't cut it.