The broken oiler was my fault. There's a large "washer" that goes between the oiler and chain brake. I didn't put it on before putting the brake on which allowed the brake to crush the oiler.
I'm not. I didn't want to pay someone to rebuild it, so I chose to go the cheapest route possible. If/when I burn the piston up again, I'll replace everything since I know how to rebuild it myself.
It was preventing me from getting the cylinder out. Figured out that it was reverse threaded onto the shaft. I got it rebuilt and it runs well except for the oiler that I managed to break. Got a new one coming this week.