Items Not In my Library vs Playlist xml Match

Hi All,
I have two theoretically identical iTunes libraries on two different machines, the only difference being compression: one library is lossy and one is lossless. The number of tracks in both libraries is the same and there are no dead tracks. When I use home sharing to show "items not in my library" nothing pops up on either machine.
In order to keep all my playlists synched across the two libraries when I add tracks to a playlist on one machine, I will export xml of the playlist, import to the other library and compare the two with a smart playlist. There are certain playlists that always throw the "itunes cannot find all of these tracks" error, but if I use Home Sharing and look at the playlist on the other machine and select "items not in my library," there aren't any.
There also seems to be a difference between how the two libraries "view" duplicates, which may have something to do with it (or not), but this difference only manifests itself with playlists. When I "view duplicates" the number is the same, but when adding tracks to a playlist via the above method the smart playlist on one machine or the other will think that a track is already there when it's not, and it won't get picked up as not being on the playlist being updated or won't make it onto the playlist that the update is coming from.
Both versions of iTunes are 12.0.1.26, both Macs running 10.9.5 (one 2 year old MB Pro, one 2 year old iMac).
Any reason anybody can see why this would be happening? Any suggestions for how to achieve these results in a less labor-intensive way?
I = all ears.
Jack

Ha! Uncanny! How the **** did you know about Teddybear's Picnic? It's just the play counts, I don't use ratings and I've pretty much appended everything else to the tracks themselves. I'm pretty close to having listened to both libraries all the way through (at least one "play" each). Once I get there I won't care about play counts any more, but I'd hate to bail out on the project now.
I just think it's odd that one library sees a track as missing from a playlist but not missing from the library and wonder why that might be, or if there's some heretofore unknown preferences controlling what counts as duplicate information in what instance.

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Items Not In my Library vs Playlist xml Match

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