Discrepancy between playlist on iPod and iTunes

**reposting this here as I don't think this problem is specific to iPod Classic**
I've selected all the music I want and put it into a playlist in iTunes. This list contains 16127 items and is 145.79GB (so, within the capacity of the iPod classic). I now want this music to copy, via sync, to my device. The problem is that it doesn't seem to believe the playlist is as big as it is. Whenever I go to "Music > Sync Music > Selected playlists > [my playlist]", "16082 songs" appears next to "sync music". If I do a full sync, which takes a while, obviously MOST of the music copies. But 55 items are missing somewhere. Weirdly, if I look at the playlist as it appears on the iPod (under "Devices"), rather than in iTunes, it is shown there as containing only 16082 items as well.
Since the list is so big, it's not practical to scroll through and compare both to find what is missing.
But does anyone have any idea what is causing this problem? How could I fix it?
To be clear, here is what I see in the status bar when I click on the playlist in iTunes:
https://www.dropbox.com/s/ly1rn982vl2s5is/Screenshot%202014-05-28%2002.51.30.png
And this is what appears when I tell it to sync with the iPod:
https://www.dropbox.com/s/1lyvspyagkbrhls/Screenshot%202014-05-28%2002.51.58.png

There are a few reasons why this might happen.
You could create a Smart Playlist in iTunes that includes anything not in your iPod Playlists. It would look like this:
and it should have all the missing items.
Note my use of the word "items". You may find that the missing items are:
Podcasts
Unticked items. Notice that my Smart Playlist does not have the "match only ticked items" turned on. So the Playlist will includes items that are not ticked. You may have put unticked items into your "iPod" Playlist, but if you have Sync only ticked songs and videos checked (turned on) then those unticked items would be in the Playlist but not on the iPod itself.
So start with the above.
What is in the Smart Playlist? Are they Podcasts or are they all unticked?
Alternatively, is there anything else common about the missing items?

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Discrepancy between playlist on iPod and iTunes

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