TS1718 I can't get iTunes to simply play the next song on the list

I can't get iTunes to simply play the next song on the list. It simply stops after playing one song.

That's consistent with all the tickboxes to the left of the tracks (in Song view) being unchecked.
Go into Song view and Ctrl-click (on Windows) or Command-click (on Mac OS) one of the empty boxes to do a "global recheck".
If you can't see the tickboxes, head into your General preferences tab and select "Show list tickboxes" as per the following screenshot (it's for an earlier version of iTunes, but the boxes are in roughly the same place in the recent versions 11.x):

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