I got the regulator back on the bike and based on my notes from the tech at Rick's I did have it installed correctly the first time. I took the switch apart, and while it wasn't really dirty it's functionality and condition was somewhat suspicious so I ordered a new one. In the mean time I put a simple heavy duty toggle switch in it's place, mostly because it was 60 yesterday and I wanted to ride.
Unfortunately, it was not charging the battery yesterday. (on the plus side, no over voltage either) I started out at 13.2v fresh off the charger. It was sitting at about 12.8 when the bike was running, and the voltage slowly dropped over the course of my ride to low 12v, high 11. According to the app my headlight is the biggest draw, and shutting that off provides a bump but the trend was still downward. There isn't any surge in voltage when twisting the throttle.
Now what?
Cooked battery? Stator? Wiring shenanigans?