Sync both Watched and Unwatched shows - possible?

I have four episodes of a show I want on the iPhone all the time. These are the only episodes of the show I have.
I also have three entire seasons of another show I want to watch in order.
Is there a method using smartlists or some other workaround that will allow me to sync the Least Recent Unwatched episodes of the show I have multiple seasons of and also sync the four watched episodes of the other show I want on the phone all the time?
I've been digging around a bit and am not hopeful of a positive response to this but it doesn't hurt to ask, right?

Since I posted this, I have discovered the menu in iTunes that allows you to choose between syncing TV Shows or syncing a Playlist. I created a playlist and populated it with the unwatched episodes of the show I have multiple seasons of (5 at a time) as well as the other four episodes of a show I have already watched but want on the phone all the time.
This solves my problems but is more labor intensive than I hoped for. So let me change my question a bit: Is it possible to make a smart-playlist that is populated with only the 5 oldest unwatched episodes at a time? I cannot figure out the boolean enough to make it work.
If Episode number were an option to choose episodes by, I could populate the smartlist with unwatched episodes selected by episode number. When a show was watched, it would drop off the list and the next episode would fill in.

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