1. For the flywheel/starter, I'm going to leave to others. It's getting weird. I.E. 139 flywheel teeth and shaft on starter was 1/2". Had a 6V battery in it. Teeth seem OK. It's remotely possible that someone made some sort of hybrid starter.
2. Sounds like you have a gravity feed to the carb intake. That will work. When you said "pouring gas straight into carb", thought you meant dribbling down the throat of carb.
3. Your motor and truck would have a mechanical oil gauge. Which is a tube from motor to gauge. Not a wire. You also probably have a filter/cartridge canister. The pic shows a copper line at lower right. This is where you tap into the pressure for test gauge or permanent gauge install. There is a Tee fitting going into block, one port for filter, one port for pressure gauge.
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