Why aren't all tracks in playlist syncing to iPad?

Even though I'm using Atomicparsley to tag each file with unique attributes like this

$AP "$dirname/$basename" --metaEnema \

--TVEpisodeNum $epi \

--title "$epi. $basename_without" \

--TVShowName "$show" \

--TVSeasonNum 1 \

--TVEpisode "$show-$epi" \

--stik "TV Show" 2>&1 > /dev/null

Where each file is guaranteed to have a unique set of the above attributes include the filename itself which has the episode number.

I can see 1800+ files in the Smart playlist in TV.app but it only syncs 1400 to my iPad.

There's some de-duping (or so it thinks they are dupes) preventing it from syncing all tracks to the iPad.