It has a carb issue - you had to hold the throttle open to start it because the crankcase was flooded with gas - gas pouring out of the carb was a sign that the carb was having a problem and not controlling the fuel level inside the float bowl.
That is what I thought at first, but even after draining the crank case, and checking that the carb was starting and stopping the flow of fuel, letting things air out/dry out, it still wouldn’t start. And didn’t sound like it wanted to at all. My next guess was that the base gasket was blown out which ended up being true when I got down to the cylinder, so again, I guessed the flooding did that?It has a carb issue - you had to hold the throttle open to start it because the crankcase was flooded with gas - gas pouring out of the carb was a sign that the carb was having a problem and not controlling the fuel level inside the float bowl.
I’ll definitely get the base trued. That’s an excellent point.OK - well yeah, you had multiple problems - the head was under torqued, that didn't hurt anything, just needed re-torqued. The cylinder was under torqued or over torqued - if someone had removed the cylinder, installed it and didn't get it tight, then crankcase compression blew out the base gasket - if the cylinder was installed, the base gasket re-used and then the cylinder over tightened, the base of the cylinder may have been warped and installing with a new gasket could cause the base gasket to blow out again, but if the cylinder base was warped and the gasket loose between the bolts and the crankcase filled with gas, then it may have been gas that blew out the gasket. I have seen crank seals blow out from the crankcase being full of gas.
Since the cylinder is off being bored out, I would run it by a machine shop and have the cylinder base trued. A machinist would chuck it up in a lathe and take a few thousandths off the gasket surface to make it perfectly flat. That would eliminate the possibility of the ears where the base bolts tighten the cylinder to the crankcase being warped and assure a good seal.
Sounds like you have it under control.