[Osage Orange]

Your timing gear shouldn't wobble or be eccentric. Something's going on there, and I suspect it is misaligned on the shaft. You may just have to remove the pulley and the front cover, get in there and find out why the timing gear is at an angle and fix that.
Now, if it started up and then died, not once but twice, I'd start at the fuel bulb and petcock and work my way toward the carburetor, making sure there isn't something intermittently clogging the line or the mesh strainer, then pull the carburetor, check the float level and all orifices and needle valves, blow them out with brake cleaner, carb cleaner and high-pressure air.