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At this point I would obtain solid core ignition wires and make up a set of 6, stuffing the ends of the wires into the shielded spark plug and the ignition tower. This will eliminate the wires. Weak spark outside of the cylinder will be even weaker under compression. Should be a loud SNAP...

Start back at the basics. Have someone crank it and put your finger over the #1 spark plug hole and see if the #1 spark happens when the compression blows your finger off the hole.

Good catch on the oil level. For sure if you have an old crusty diaphragm in your fuel pump, gas will end up in the crankcase. Fix this before doing anything else. The soot on your plugs means overfueling. Stuck valve would be a horrible engine miss.

Any time it won't start, remove the plugs, reattach to the wires, crank it and verify you still have a hot blue spark on all 6 plugs.

that last scenario sounds a lot like stuck carb float needle valve causing a flood.

No ideas here but what I would do in your situation when it won't start is to remove all 6 spark plugs and reattach the cables and see if you have a nice blue spark at all 6 plugs.