IPod Video - iTunes - iPod Options - Videos - All options grayed out?

So how do I get this so I can use it? Right now, I can only get videos on my iPod by dragging them onto the iPod (e.g. an iPod only playlist).
This iPod options tab implies I could sync up using a directory, like with photos.
Am I missing something?

I mention Photos only because that works the way I'd expect - I tell it to sync with the "Pictures" directory on my hard drive, and every time I plug in the iPod, all new photos are sent over without me having to do anything. (Although it would be nice if photos handled more than one directory deep when browsing on the iPod, but since it's fast, it's good enough).
I've got a directory on my hard drive called "Videos-Portable" that I'd like to point to, and have new videos transferred each time I plug in the iPod, preferably with at least one directory deep (like Photos).
Music I can just copy over as I want it, since that's actually my least use of the iPod. But I'm willing to set music up so that I can get the videos sync'd the way I want (like the way Photos works). I just transferred a couple thousand songs over to the iPod, and given the iTunes question that popped up when I attempted to switch the synch type (and then cancelled), it sounds like it's going to delete all the music I just transferred, but I'm willing to do this once again if it means I get what I want from Videos.
Makes sense?

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