Why do my playlists no longer sync reliably with iPhone?

Having used iTunes and various devices without difficulty for 8 years, I've only now encountered playlist syncing problems between iTunes and my iPhone 5. Random songs are missing from random playlists. The songs are transferred to the device but do not appear in the playlist. When they are manually added in the device, they dissappear at the next sync.

I am having a similar problem; only with the last few syncs to my iphone 5S (lastest iOS version) with 11.1.4 version of iTunes on MacBook Pro.
The problem seems with small playlists where I have downloaded 1 song on my iphone and the other on my MacBook Pro - only the song downloaded to the MacBook will sync with iphone 5S - the one downloaded to my phone transfers to music library but won't sync back to iphone from playlist created on MacBook.
But, an album I downloaded to Mac and added to a playlist synced with iphone first attempt = no hassles.
iPhone 5S; iTunes 11.1.4 on MacBook Pro Retina; iOS 7.0.5

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