@tyguyc welcome here!
After all this read:
-100% sure the exactely same cylinder?
-piston rings reused and maybe not turned properly horizontally to avoid blowby (blue smoke)
-head gasket blowing (compression test?)
-once again check timing marks when at TDC
-sparkplug wet from fuel
-sparkplug out and check sparking
-check carb again
One more thing came in my mind:
You said you replaced your carb.
Your carb is fed by a vacuum fuelpump, where there are three hoses. (pls see pic)
One IN from fuel tank, one OUT to your carbs float chamber and one more, which is the vacuum TO/FROM carb, line. Maybe there is something wrong with tubes or this diaphragm is faulty.
Pls give a feedback for us to learn
Thank you Sir Ruffus. The fuel pump is out of the equation. I temporarily capped the vac ports and filled to bowl. (but it does work)
-100% sure the exactely same cylinder?
No but over %95.
-piston rings reused and maybe not turned properly horizontally to avoid blowby (blue smoke)
There is some blue smoke, but I believe that is the new head being in worse shape than my old head. But I realize it could be both.
-head gasket blowing (compression test?)
I did a DIY job to flatten the mating surfaces and the MLS Gasket was in decent shape. I didnt break out my compression tester but it is making good pressure.
-once again check timing marks when at TDC
Double checked and actually went one tooth advanced to try and get that intake valve to close sooner.
-sparkplug wet from fuel
checked and yes.
-sparkplug out and check sparking
checked good
-check carb again
I did plug in the old carb with the TPS Sensor and didn't make any actionable difference, but I also put 1-2 mL of gas down the intake and that didnt have any effect either.
What can cause these kinds of engines to have a hard spot in the rotation? The starter seems to struggle in one area of rotation and I wonder if thats my root cause.