Syncing with iphone not completely...

iTunes seems to struggle with itself:
I've got my music on 2 Computers: one at home, one at work.
The Libraries are very similar (the one at work is the child), with about 95% of the files being identical.
iTunes match is enabled, so play counts etc. are mirrored.
Both computer run OS 10.9.4 and itunes 11.3. On the iphone 5, IOS 7.1.2
ITunes allows me to sync from both computers to the phone without complaining or threatening to delete everything. This suggests it is ok to do so, not?
BUT: The playlists I want to sync - most are simple-made dynamic playlists that get updated upon syncing - aren't updated correctly. My favorite one contains 48 tracks, itunes indicates they are on the phone, but they are not there (or they're not visible):
This is how it looks on the mac (at work):
and here's what the phone reflects:
these are all files in the playlist (on the phone)
What could be this?
Thanks in advance!

First of all, your post title refers to an iPhone 5S.  There is no such device being sold by Apple.
Aside from that, it sounds like your contacts are in more than one account on your Mac.  In Contacts on your Mac, you might try clicking the button closest to the plus side in the lower left of the display to hopefully show your various accounts.  You might also check Contacts > Preferences > Accounts.

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