Went back over everything today with a clearer head, and results are the same. I have the proper voltages from the outlet to the transformer, from the transformer to the bell, from the transformer to the button.
The Ring doorbell cam is still dead. Doesn’t power up at all, charged it for a few hours and checked it again. No lights, no nothing, did the hard reset on it again with no results.
Sucks that it died a month after the warranty expired…