Older engines can leak water into the cylinders if the head gasket leaks around the #5-#6 cylinder and the rusted water jacket ports.
Some old blocks are so rusted, decking the block flat is impossible, where the water jacket seals the head.
AuroraGirl's recommendation to pull the plugs carefully and take a picture of each one, then post them here.
If the water jacket ports are rusted and gouged into the deck surface, OEM gaskets with a very wide fire ring, leave very little room for a seal.
If your piston is sucking in water, this would explain the starter finding a sluggish spot and the timing issues, starter kick back, etc.
Coolant will not comprress.
Compressing coolant can break your Starter Bendix and break ring gear teeth.
You MAY have to pull the heads and take a picture of the deck.
If there's a 1/16" rusted gouge around the water jacket port area near cylinders #5-6,
You might have the dreaded "Hydro-Jerk" AuroraGirl warned you about.
Last thing anyone wants (or needs) is a: "Hydro-Jerk"- AuroraGirl Copyright