Learning about setting the timing caused me to use the starter a bit more than normal. Nothing crazy and didn't over heat it. Probably 5sec or so cycles and 15 total times.
It started making a loud metallic sound so I stopped. The CNC adapter was slightly loose against the starter motor. The bolts holding it to the gear box were nice and tight.
Is it in the correct orientation? The flywheel teeth look to only be about 20% engaging.
Trying the other position hits the gearbox and I would have to remove material from the starter motor.