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If you have all new, "working" and "tested" parts, then look at the flywheel key.

Does the engine die suddenly like you turned the key off (electrical), or kind of chug a bit and come to a halt (fuel)?

Was this an OEM carb or a Chinese Scamazon/Fleabay clone?

Just pull the hose off AT the carb inlet. Drain into a glass jar. Will easily see if the pump or a gravity system is working or not.

Where are you getting these regulators from? Think I know where....... And having to move some pins around doesn't sound normal. Get a...

You need to quit jump starting it and put the battery on a charger to get it fully charged. Fortunately, you have not burned up the...

I know you verified the ground connection, but I'd make sure the negative end of the bat cable is nice and "tight" where it connects to...

Shouldn’t the higher rpm show a higher voltage output from regulator to battery?

Charge the battery to 12.75 volts, then check to see if it is charging. System will not charge a flat uncharged battery.

Buy the proper OEM belt.

Can it fail, sure. Needing full choke to run is a dirty carb and or lack of fuel delivery. Possible fuel tank vent failure.

That white fog looks to be atomized fuel. As in the needle and seat not sealing proper.

So I'm on my phone and I took a picture of the image it's definitely a blown head gasket I've seen others were where gets ruined and...

THAT is definitely blown. No question. Now is the fun part. You must clean and lap the head and area on the block where the new...

Blown head gasket image.