IPod Syncing not syncing the videos I want

It seems as though iTunes ignores my option of "Sync 5 least resent unwatched episodes..." all the time. I end up getting shows Im not ready to watch yet. It seems like the "new" and "not new" markers are ignored.
Also, I have 2 seasons of a TV show purchased from iTunes and when I use this option to sync, it puts the first 5 shows from Season 2 first, even though I havent watched Season 1 yet.
I dont know if anyone else is having syncing issues like this one, but there is definitely something glitchy going on here that shouldn't be!

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