Engine Starter meshing issue after hard starts

So I have had countless issues with my motor swap, there seems to be light at the end of the tunnel but here we go..

308 with 11.5:1 compression, professionally built engine pulled from another car I just dropped into my '88.

Initial startup with the stock starter worked fine, it struggled to turn the engine but it worked good enough until I could get a PMGR starter delivered.

With the PMGR installed, it made a terrible grinding noise as if the starter and ring gear were not meshing properly. (Still started the car)

Took the PMGR off and out the stock back on until I could try another PMGR (figured it may be faulty)

Stock worked fine until a couple days ago when I tried to start it with 4/8 plug wires connected by accident (oops) and ended up flooding the engine causing a few hard starts and kickbacks on the starter.

All of a sudden the stock starter starts making the same grinding noise the PMGR did, as if the gears arent meshing.

I thought maybe I ruined the stock starter (probably on its way out anyway) so I put a close-to-new stock starter back on and it makes the same exact noise.

I can see the teeth on the flywheel are a bit chewed up from the Hi torque, but nothing serious. I cant imagine that would cause it not to mesh. Although, it does still start the car.

I am at a loss and really dont want to have to replace the flywheel. Everybody is telling me this issue lies on the ruined ring gear teeth.

Any help would be appreciated!!!

Thanks
 
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Here is the flywheel on the car and the comparison between the stock and PMGR starter
 

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What other car was it from and is this the flywheel and bell housing from that same car?

It is the bellhousing and flywheel from my old motor. I believe both of these are working fine with the motor application though as the starter worked perfectly fine up until a couple days ago.

Although, I noticed last night that the lower starter bolt hole is stripped out and will not tighten fully. I only noticed this just now.

Would this cause the starter to be kicking back away from the flywheel if it isnt fully tight?

I imagine it would.