With Apple’s push to deliver video on more and more portable devices, I’m surprised that I haven’t seen this complaint yet.

Maybe I’m not looking in the right places. I love watching video on my iPhone. I also have a few season passes to TV shows through the iTunes Music Store. Some shows, like my new favorite Dexter, don’t release any episodes until the entire season is available. Here’s where the problem comes in. The first season of Dexter is 14 episodes, each around 660-670 megabytes in size. I have a 4 gig iPhone, so there’s no way all of the episodes will fit. Luckily, iTunes offers some flexibility in how video is synced to devices. I can select to sync all unwatched episodes of a show, or a subset of 1, 3, 5, or 10 unwatched episodes. For some reason, though, I can only pick the most recent unwatched episodes. WTF? Why the hell would I download an entire series, then choose to only sync the last 10 episodes? Why on earth didn’t Apple put in a similar set of options to let me sync the first 1, 3, 5, 10 episodes?

As it stands now, I have to watch enough episodes on my computer or my video iPod to be able to sync remaining episodes with the iPhone. I can create a smart playlist that keeps track of the oldest X number of unwatched episodes, but it doesn’t sync to the iPhone. iTunes sees the playlist as belonging to the Music category, and I can only choose to sync music videos, not TV shows within playlists.

C’mon Apple. I know this can’t be too hard. Make it easy for me to watch video on my iPhone like all the hype tells me I should do.