Storage space on an iPhone is at a premium. There just isn’t enough space on it to be able to store an entire season of a TV Show that you’ve ripped from the DVDs you bought. But then, there shouldn’t really need to be - most people will only need or want to watch a couple of episodes of something between times that they’re able to dock with their home machine. So, it would make sense to be able to just sync the next couple of unwatched episodes of a few shows to your iPhone, iPod etc. You’d think you’d be able to just do that with iTunes, wouldn’t you? Unfortunately, out of the box you can’t.
What you can do though is run a little AppleScript voodoo that’ll do the job for you. Installing the script onto your system will take at most five minutes, and then you’ll simply have to run the script before you sync your iPhone so that it knows which episodes need syncing.