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Yep, Looks like your initial assessment was correct. In picture of bell housing oil is dripping and all other location dry.
 
I wonder if the transmission was ever worked on/replaced? Maybe they reinstalled the flex plate wrong or it needed to be replaced due to warping?
 
Hard to see in pictures. But bolt of transmission cross bar, don't look removed. Did you remove inspection plate while on the road or was it off?
 
You can spin crank while looking at flex plate. You may see crack. Also one bolt is black so you know when you've turned 360deg.

You can also drain oil into/through a rag. Then fold rag and clean in solvent. Then open rag and look for metal.

If HM oil (high mileage oil) used for two oil changes, it must always then be used. It has a petroleum based seal modifier. This is damaging to seal.

Oil dip stick indicated oil not change enough and hot. Not good.

Looking at carfax and Toyota history, you may get indication of oil changes. Also doing and oil pressure test will gives clues to crank and bearing health. If you bad or spun a bearing oil pressure will drop. Vibration of crank could loosen seal.

Compression test should also be done.

I'd do a lot of test on engine like this before sinking to much time and parts.
 
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OK, you sure it's oil that was leaking from the back of the engine, not just old, dark trans fluid? Possibly the trans front seal sprung? That will make a big mess.... Did you check the oil when you bought it, you're sure the 2 quarts low happened when you were driving, it wasn't already low when you bought it?

Maybe stick a piece of clean cardboard under the area and see what/how much is actually leaking. What you are describing as 'zip ties against the flywheel' could describe a really bad torque converter, too.
 
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I checked the engine oil at 0 and 100 miles of my drive, and it was a bit overfull both times.
Definitely leaking engine oil, absolutely not tranny fluid, and it leaks significantly from the rear main area when running.
Yeah, you got me. Time to start taking stuff apart if you are leaking that much from the rear main.
 
I have a minor rear main seal leak as well, i hope they don't just fail like that if that's your issue as well.
 
I bumped the starter to move the flex plate, looked ok, but I can’t see the flange where I think it has sheared.
If sheared off, It wouldn't drive, as there be no power to transmission. I wouldn't think, that by itself would not cause sudden oil loss. Guys that have had flex plate fail, just got a lot of vibration as RPM raised. They get a crack that can be seen from below, sometimes. It appear usually where flex plate start to curve/bump out. It's hard to see. But turn crank with a socket and ratchet at found crank bolt that holds harmonic balance. With flashing, look as deep as you can up in flex plate. In your fist picture you can see the curve.
 
If sheared off, It wouldn't drive, as there be no power to transmission. I wouldn't think, that by itself would not cause sudden oil loss. Guys that have had flex plate fail, just got a lot of vibration as RPM raised. They get a crack that can be seen from below, sometimes. It appear usually where flex plate start to curve/bump out. It's hard to see. But turn crank with a socket and ratchet at found crank bolt that holds harmonic balance. With flashing, look as deep as you can up in flex plate. In your fist picture you can see the curve.
Is it possible that a piece of flexplate broke off and punctured or cracked the oil seal retainer cover? I've not held that part in my hands, so don't know how burly it is or what it would take to break it...
 
I think your decision to drive a Copart car home sounds like adventure more than a poor choice, haha! I used to flip non-running cars and it was always an adventure. Some of my favorite car memories came from that time and the "bad decisions" were some of the most memorable.

I'm anxious to see how it all turns out. You don't see too many catastrophic failures on these, so when it happens, it's pretty interesting to see.
 
Is it possible that a piece of flexplate broke off and punctured or cracked the oil seal retainer cover? I've not held that part in my hands, so don't know how burly it is or what it would take to break it...
Possible, but not likely, based on pictures in OP. Also statement, the it was not metal but gasket sealant (FIPG). Had flex plate come apart like that at high RPM, it could fly apart. It's been many years, but I recall one flex plate reported in mud as bad. He had the "D" vibration IIRC.

I'm anxious to see how it all turns out. You don't see too many catastrophic failures on these, so when it happens, it's pretty interesting to see.
Me too for a number of reasons. One I just inspect a 2006 with oil at rear weep hole. Two these seems to be very usual.

Be interesting also to see if VIN # on engine is a 100 series and what history of it is. This almost sound like a busted rob on #8. But I'm not sure it would run in that event.

Bunch of metal in the filter, looks like the engine’s gonna be coming out.
Anyway @PNWFJ80 is out there rooting around digging deep. He'll have something for us soon. Just as I was typing. This could be a busted rod. Check that VIN # on the head. Is this matching?
 
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