Glad I wasn't guessing wrong
Ok, log file attached. Haven't made any changes to the plugin settings in a while. I usually open Calibre once every day or two to sync reading position, etc.
Grabbed a screenshot of settings. (I've tried with and without "Only if newer", no different behavior)
I realized something new this AM. I ran the GR update and noticed that on connect, I'm now not even pulling in an updated reading position from the device.
No factory resets have been done.
Edit to add: Thanks!