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That is a great write-up, the only thing I can think of to add is to take a small pry bar and after removing the last converter bolt to gently pry the converter towards the transmission to make sure it is released from the pilot in the crankshaft so the converter comes back with the...

Is the face of the flex plate teeth flattened out enough to interfere with the bendix engagement? That is what I would suspect, a little work with a small triangle file might do the trick, it does not look like that much tooth missing, not ideal or pretty but much less work.

About 2/3 is actually normal it appears looking at a couple starters that I have, the bendix teeth are wider than the flex plate teeth

Sounds like all you need is a GOOD switch and another starter :(

I think what he was eluding to was that the cheap switch was partially energizing the starter all the time which caused at least the second starter to fail as it was engaging or at least trying to engage the bendix all of the time. The second starter is now damaged, no switch is going to help it.

BTW which one did you go with, the new one or the rebuilt one?

Everything else aside, if that bendix cannot even be pushed back at this point you have a mechanical issue with the starter.

Does seem like that starter failed if the bendix will not retract, that bites!!

Well that is certainly possible, it would explain why the voltage was not dropping as much as I expected. Glad you got her going!

The last time it ran,,, was there anything unusual about the way it ran or when it was shut off? I would say 25V at the starter would be pretty good, in fact maybe too good like the starter is not loaded as you would expect, of course as Coug pointed out do a voltage drop on the negative side...

The "shimming" is also not an issue, when there is an interference issue on a GM starter the bendix will tend to not retract. There is a large solenoid shoving the bendix into the flex plate but only a spring pulling it back, that is what gives the awful screeching on an improperly shimmed GM...

That amount of engagement is perfectly normal, would be very difficult to install the flex plate backwards.

Or possibly a bad starter but I would look at everything else really close

The starter is engaging that is not the problem, something else is wrong, not enough juice or an engine problem. Measure the voltage AT the starter (pos and neg) when trying to start. IS that the same sound/symptom as before?

I ordered enough stock to make a ton of them, you need to be able to tighten that nut while holding the key, tight enough that it will not get loose. I sent you a PM

I was having problems finding the core nut tool, looks like they expect you to make one.

Actually after thinking about it, I would replace that fork, it is just as important to pull the bendix back as it is to push it forward and any wear limits the overall travel.

You may have to buy a new solenoid to get the seal, not a bad idea anyway.

It looks symmetrical, that means you can install it the other way around and start with a virgin surface

Also pay close attention to the shims, there is usually an insulated shim directly against the commutator and then there may be bronze shims between the insulated one and the rear bushing and there is a bronze shim between the collar and the nose piece. Do not use emery cloth on the commutator...