Update, I pulled the head off, the two bolts on the exhaust side were loose compared to the other side. there was WD40 in the cylinder, which must have leaked in past the gasket when I was turning it over trying to confirm the leak. So the gasket was definitely leaking, see photos. I was in two minds, fit a new gasket and put it back together or strip it down and do the rings as well. I pulled the fly wheel off. The key is sheared and the flywheel has been moving on the shaft. This thing was running (sort of).
You guys have been great so far, so do I keep pulling it apart to do the rings or fix the keyway and head gasket only, which im sure will make a big difference.