How can the album-art, which is all in iTunes , suddenly only shows partially on the iPod classic 160 gb?

I'm user of iTunes for years and in possession of 2 iPod classics.
For both iPods I have a specific playlist created, which I sync with iTunes. Each of my nearly 50,000 tracks in iTunes comes with the right Album-art (all 500 x 500 pixels and 72 dpi) andeach track contains also the necessary meta data and is converted to 160 or 192 kbps  M4a. In Finder on my MacBook I can see that the M4a files all contain album-art, because the file icons show the album art for each file name! Also in the grid overview of iTunes you can see them all, no exception.
For years that went well. Now,  a week ago, I made a new playlist (16,000 tracks) for one of my iPod classics because I wanted a different content! The old playlist I discarded and synchronized the new one.  Now it appears that a large number of album-art on the iPod is not shown, nor in cover-flow nor during play-back. I then tried to get my new playlist updated by exported as XML and then imported into iTunes again. In that case all tracks from the list are checked for completeness against the library and after import it should be fine. Unfortunately, it is not the case. Still the album-art is not shown for all tracks/albums on the iPod.
I run iTunes (11.2.2 (3)) on a MacBook Pro at the end of 2009, with the latest OSX version (10.9.3) and with enough disk space and memory.
My iTunes library is on a NAS (Synodisk DS209J II plus) the iPods run on the latest sw version (1.1.2) and are both Apple formatted.
I wonder if this is an iPod error or something wrong with the library. I hope you will understand, that I do not want to lose all the metadata of the 50,000 tracks by rebuilding the library, especially things like: date added, number of times played, rating, comments!
I hope someone can provide me an acceptable solution.
With regards, Sign-X

I'm a bit confused, but I assume you want to shuffle your playlist while you are playing it in iTunes. If this is so, you will actually have to start playing a song before the shuffle button appears, and it appears in the top center panel of your iTunes window. Yeah, I know...

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