So, Barry’s inspection of bug reports indicates that there is a problem with one of more of your extensions. What happens is SketchUp rewrites the JSON files during it’s shutdown cycle.
Apparently (educated guess) the JSON rewrite is being interrupted or corrupted by some triggered bug involving the Ruby API, we presume by one of the extensions that you have installed.
In Extension Manager, switch OFF all extensions, except those that come along with SketchUp. (I.e, Dynamic Components, Add Location, and Sandbox Tools.)
Restart SketchUp.
In Extension Manager, change to see if any of them need updating (via the Manage tab.) Update them and restart if any do.
Otherwise, switch on a small group of extensions at a time for testing, to narrow down the culprit(s). Restart after switching them ON.
Test.
Repeat, by switching on another small set of extensions, and test again.
In this way, see if you can determine which extension may be interfering with normal SketchUp shutdown (which, as said, is perhaps interfering with normal rewriting of the JSON preferences files.)
(Musing) One of the recent changes in the past few cycles, was that multi-threaded SKP file saving was added. Just a hunch, that perhaps a extension saving either the model, a copy of it, or some other extension file could be triggering whilst SketchUp wants to rewrite the JSON files?
Actually I have been having repeated issues with the JSON file corruption in the past 3 versions since the SketchUp Windows edition began migrating to use the Qt GUI libraires. (Starting with version 23.)
I also have been having repeated problems with custom templates in these same versions causing crashes.