Hmmm, barring a nasty coincidence, does sound like timing is your current nemisis:
Rebuit, let's assume it's all tight. This also means, you can pull the valve cover and make sure you're not 180 out and your wires are in order too [1,3,4,2]: exhuast: open, close, intake: open, close, and about half crank after that closes until you have the TDC mark in the window.
With TDC, your mag should be on which ever cylinder you set and the points just opening. The rest will be closewise around the mag in firing order (or watch the valves as you connect each, if you prefer).
As to the original beast, I want to guess it's sucking air at the carb gasket or the manifold gasket; or maybe the carb is misbehaving. Unless something else is way wrong (valves timed wrong) or head gasket or something else isn't keeping compression, I don't know why it'd start so easy with assistance and not at all on the crank. Perhaps, timed wayyy too late would have done that too.
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