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It looks good. I also see that the pan bolts were not overtightened, a good thing. Yes, the starter must be removed to take the cover off. I've known of people who cut the cover so that it can be removed without disturbing the starter.
All of them have a dust or gravel shield. The inspection cover was a small piece at the bottom of the dust cover to allow access to the converter drain plug 68-74 or so.
All above are good thoughts, except, the problem was first found after draining the 1 1/2 quarts, according to my reading of the original post. How would that crack the flex plate, and suddenly, it seemed, to cause the squeak? It did not squeak before the draining.
The OP holds the key by...
First, let's get the events straight,
You drove this for a while with no offending noises?
You checked the fluid level properly- car level, engine warm, at idle, in neutral?
Or did you check with the engine off!
It showed really high, and you removed 1 1/2 quarts.
The immediate result was a...
My recipe for a "kit"
Gasket, seal kit
Bushings (drivers Amazon 52 piece, $50.)
Be really picky about the fit of the front pump bushing.
Front, direct retainer- 5 thin red frictions- good, used steels (forget the Kolene scam).
2 1/4-inch red solid band. Not flex band.
3.8 or 4.2 lever (5 to 1 is...
After the VB checkup and band adjustment, was the transmission sealed up really good with RTV? I mostly try to avoid the stuff. Bits of it find their way into the oil and goof up the valves. I suspect that some got into the governor. That might account for the changed shift points.
I've found several core plugs in engines, lost, probably like yours. Do not worry about rust, as I'm sure that you'll use antifreeze with anti-rust ingredients. Overheating- I really doubt it. If you are really vexed about it, a cheap borescope, about $50- $80 will probably allow you to see it...