Your distributor looks like a replacement unit that is available all over the internet for prices from about $65 to $290. Presumably, it is a drop-in replacement that should behave the same as the original. The details that have been posted here such as those relating to how the gear is mounted etc. may not apply. It probably has a 24 degree advance rather than the 16 called out for a Cub. But that is the least of your problems right now.
Are you saying that EACH of the above pictures was taken with the notch in the pulley in line with the timing pointer? The rotor should turn at EXACTLY one half the speed of the crankshaft. When cylinder 1 is at TDC compression, the rotor should be pointed at about 1 o'clock. If the crankshaft is turned one full revolution, the rotor should then be pointed exactly the opposite direction to about 7 o'clock. One more crank revolution should bring it back to 1 o'clock. If that is not what is happening, there must be some failure in the mechanical drive from the crankshaft to the distributor.
If you are not getting the exact 2:1 ratio, pull the distributor back out and post a picture of the gear on the bottom of the distributor. If that gear looks good, pull the distributor adapter (which does the 2:1 speed reduction). See if there is a problem with the gears/shaft in that area. When it is removed, the shaft in the front of it pulls right out (usually falls out if you point it down). It has the gear that drives the distributor. Post a picture of it.