Just bought a 1931 Tudo! Having starter issues.

Flywheel is direct to crank. So the engine must turn over for the flywheel to turn too, it does not free-wheel.

Although from the picture you posted the ring gear has some wear on the inside, it should have engaged if that is the area it was sitting when you tried to start it. Have someone crank the engine over and look at the teeth on the ring gear.
 
To remove the Bendix, just bend the lock tab on the very end of the shaft and remove that bolt. Slide the drive head off, then remove the half moon key, then the rest will just slide right off.
 
It's a cotter pin and it's suppose to be in there to keep the drain
hole from plugging up .

Bob
 
The metal piece hanging out of the bell housing drain hole is supposed to be there. It is just a big cotter pin, installed from the inside, and it's purpose is to wiggle around, as the car is driven, to keep the hole from clogging, to allow oil, which migrates out of the rear main seal, to drain onto the ground. If the oil can't get out through that hole, it could wind up on the clutch surface, causing trouble.
 
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