I've found another strange quirk with this while doing something unrelated. If it's a book I'm deleting from the Voyage and reloading, I can save the original .azw3f file and add
only it back manually with the reloaded book and then About This Book on first opening will work! I'm baffled. It doesn't seem to make sense.
However with that I can fashion a sort of odd ghetto workaround to make everything work, involving adding a random old file to make a new book feature work and going to goodreads to make a book search work.
I would still like to understand why some books require this for these things to work and others don't. If it's something I can fix about the book while it's in Calibre that'd be preferable to the workaround.