Trouble playing old songs in the library

I can shuffle the songs I added recently but shuffle never plays the old songs. When I click on a song it plays fine and then jumps to a new song. If I turn off shuffle and go back to an old song, it plays one song and stops. It does not continue playing whatever is next in the list. It has been doing this for a while and updating to 7.3 (and now to 7.4) did not help. Any ideas?
ps: I don't know if that matters but it is not the most recent xxx number of songs that I can shuffle. It is songs uploaded before point A vs those uploaded after that point.

Make sure that the mentioned playlist is sorted by number: Click on top of the very left column, then drag your files into the desired position.

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