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I have had this happen three times now. When engaging the starter the starter will hang up on the flywheel and stick and will not disengage. The only way to get it working again is to put a breaker bar/socket on the crankshaft and turn the motor over a little bit by hand until it pops loose, then the starter will continue to work as it should. The starter works perfectly fine 99% of the time, but after it happened again today (third time), I guess it's time to pull the starter and take a look. Any suggestions on a fix or what to look for? Any advice is appreciated. Thanks.

Sounds like the starter drive has gotten gummy and needs to be cleaned. The gear slides along the starter shaft to engage the flywheel. If that has any buildup on it you will get erratic action. If it is a stickshift car, mousies have a chance to get into the bell housing over the winter and make a nest. Ground up mouse nest is great for making starters misbehave.
But on closer reading it appears your starter engages and jams before starting the engine? Then both the starter and ring gear teeth need to be examined.

Whilst you have it out, take the starter apart and clean it and oil its three bushings. Make sure the mica on the commutator is undercut. If you feel prosperous, order a new starter solenoid and install it with clean connections. You will be pleased with the cranking speed.

I have a 51 400 and I didn't know that the crankshaft can be turned manually. Is this at the front of the engine?

I didn't know that the crankshaft can be turned manually

Absolutely. From either the front or rear, though the front is easier; sometimes just by putting a little tension on the fan belt and pulling on the fan (though be careful not to bend it), but more positively by using the large bolt holding the vibration damper to the crankshaft. From the rear by removing the cover from the clutch or torque converter and using the gear teeth and a fulcrum. Obviously, removing the spark plugs makes it much easier.

In either case make sure the ignition is DISABLED (e.g. coil wire removed) before doing it.

Hi gregb,
I also have a '51 200 w/automatic trans. Two years ago my starter engaged but did not release from the flywheel. In talking with fellow members I was directed to pull the starter and inspect the teeth of the ring gear and starter drive. I found the starter drive looked fine, still, I had the starter rebuilt (I had the car for 7 years and never had the starter out) When looking into the opening where the starter and the ring gear would meet I could see three to four teeth on the ring gear in various stages of damage....from 1/4 to 1/3 of the tooth was gone and there were sharp edges where the metal had been chipped away. I used a large pry bar and gently moved the broken ring gear teeth to a position so I could get a file in, then I filed the sharp edges and beveled the edges of the broken teeth so the bendix would more easily engage with the starter and not lock up. Reinstalled the starter, held my breath and cranked..........It works......and continues to function flawlessly. Just to be sure, I ordered a flexplate from Ross (on this forum) and have it hanging on the wall.......just in case. Hope this helps.
Steve