TV Show Sync Options

I've got iTunes 7.5 running on Windows XP. I have a lot of different TV shows, that I have sync'd to my iPod. Currently, it's syncing all unwatched episodes of every show. I'm getting close to full on my iPod. I noticed in the TV Show sync options on the iPod, it has options for syncing only 5 or 10 of the most recent, unwatched shows. This sounds great! I can keep current with all my shows, but this will allow me to have more variety of shows, without filling up the iPod...but here's the catch.
Let's use Lost as an example. Let's say I've got all 24 episodes of Season 1 of Lost in iTunes. If I choose to sync only the 5 most recent unwatched episodes, iTunes is going to put episodes 20-24 on my iPod, even though I haven't watched episodes 1-19 yet! If I do it this way, I'm going to watch season 1 of Lost backwards, in 5 episode chunks!
But I don't see an option to watch the 5 OLDEST unwatched episodes. This would make much more sense to me...
Does anyone else have this problem?

EVERYONE has that problem! Whoever at Apple decided that TV shows are watched newest first was an idiot. Instead of "Most recent unplayed," the useful option would be "Oldest unplayed." After all these updates to iTunes, we're still waiting for them to wise up.
For this reason I sync all unplayed shows BUT checked items only. I checkmark the oldest eps of the series so only those eps go to my Touch. This was the easiest way to achieve the desired result, easier than designing and nesting smartplyalists. The shows will still be upside-down on the Touch (Episode 3, Episode 2, Episode 1) but you can see which is which to play them in order.

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Message was edited by: CooperSmith

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