Well, got it all together,, Jason, i was looking in the wrong chapter in the manual on the starter,, got that figured out.  everything hooked back up

Got it put back together, started up, and oil light turned off.. putting a hole in the gasket that the oil sump filter really helped out on that..

I only ran it for ab out 15 minutes. pulled out of my friends garage, and rode down the street,,

i noticed a knock or something tha wasnt there to start with,  I think its a leak at that driver side exhaust connection.  My reason for that is, when i pulled off the exhaust, the nut didnt come off, the hole screw came out of the block,, the nut was pretty much heat soldered on bolt,  So i dont think i was able to put the 33 pounds of torque on the connection as i was afraid of stripping out the threads on the block,,   so i got it as tight as i felt comfortable cranking down on it, but it didn't hit the 33 lbs.  

Can i get replacement screws at the part store for that??

What did i learn from all this,, hmmm,, really nice to have full car lift.  

lots to look at inside the engine, but since i didnt have to touch anything there, no problems.  

the guy at arizona parts in arizona, (the guy there was quite helpful)   told me to just soak the gasket until ready, i didn't know why, but did it for the second installation of the upper seal.. it went in very nicely with no friction until the last say 3/4 inch.  i found if i pushed the tail in, toward the shaft and pushed it would go on in.  No rubber came off the end as it did on the first installation so i assume it was flush on all edges and no problems.. 

i found out that to turn the crankshaft with plugs out,, put the big torque bar on the nut on the alternator, squeeze the belt, and turn,, crank shaft turnedmoved with no problem,, so I learned a new trick there...

i cant  say this was not easy, maybe due to my lack of experience, and fear of breaking something,, but, after about 2 weeks, i got it in.. the lift really made it easier,,

i havent noticed a leak yet, but it was a very short drive and warm up..will see tomorrow how it comes out.

It cost me three rear main seals.. first one i ruined, second one fit, and the third one was a back up if the second one went bad.  so thats about 120.   (40 a piece for best gaskets from Arizona vintage parts..

oil pan gaskets,, first one i had to remove because of my oil sump mistake and had to do again,, 22.0 a piece x 2   (44.00)

exhaust gaskets  i think the was about 20,0..   

brake cleaner, assembly grease, miscellaneous stuff about 50.00, so the out of pocket parts cost was probably 230 to 250.00.

 shop wanted 550 in labor,, i know if i used there labor rate, it was a 3000.00  labor repair,, but given the learning, the advice from everyone, i came out way better,, i will know for sure how it held tomorrow.  at least i know how to do it if i have to do it again,, God forbid...

again, thanks for all the help and patience...

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UPDATE ON REAR MAIN AFTER TRIP TO SHOP

I took the car to the shop.  I knew there was a minor leak around the rear of the valley cover,  he thought once oil got warmed up, it could be source.. I said i hope.  Long story short.   That was not it.

they pulled off everything.  i explained all the things i had done, we discussed manual procedure, slide ins, of upper seal hazards and i made him aware of as many comments as i could recall to look for problem and left it to him.   He also checked to see if there was any moment in the crankshaft  forward or back,, and he informed me there was none

i came back to pick up, he said it wasnt leaking.   i said yeah!!   i said did you drive, he said they took it up the road a ways, and let it run for probably 30 or so minutes in shop.   and left over night,, no oil..  i paid him,, and said I"ll be back,, so i took the car for about 20 miles up the interstate,, 65 or so MPH,  pulled over at overpass,  no oil..  turned around,, came back,, pulled in, and yep,  you guessed it..   it was leaking,  i was deflated!! 

When i came by the first day, he asked why i had "braised" the rear semi circle area of the oil pan,  I said i didnt, it was like that..  basically, the semi circe area looked like brass, i had always noticed it, but it seemed ok, things fit, etc..  he said he wouldnt have any idea why that would be there,  there were no cracks or anything.. so he said he did his best to make it as smooth as possible with out going to machine shop, and put it all back to gather.   He was stumped when i came back in with the leak,

  He said the only things he could thing of were that oil pan is just enough out of round that its not sealing up, despite the use of silicone and RTV products.   

Secondly, he said it may be a cam seal, but he couldnt tell due to its position, and he couldnt tell from the scope he was using..   

SOOO,,, from another round of observation and despair,,,   It doesnt happen at idle or slow or puttering around town,,   it happens when you get going, and takes about 15 or so miles or minutes to get enough flow or leakthroungh to come down and be enough fluid to leak out.   What i took note of from thsi was there is no oil on the front side of the plate just behind the it is coming out the backside where the fly wheel is, there is oil on the starter again.

Now, if it IS the oil pan being warped or un smooth enough to allow oil to pass through, would that show up on the front side of the panel or the back side of the panel that covers the flywheel.  

If anyone thinks it a cam plug, how would i check that?  

any other thgouths???

Well, the oil pan was one thing I pointed out on Oct 13:
"For all it's worth it is hard to see how it would just pour oil out of the seal unless it was torn during installation, but then would expect it ti leak out of the gate. This rear seal is  basically just a rubber seal wedged up to a turning metal cylinder. I would  clean, crank the engine and get under with a good light to confirm it is out of the rear seal area.  Since it just suddenly started leaking I am wonder if it might be the rear oil pan gasket."

With that if you want a good oil pan I will have one up for sale soon. I had it cleaned and had sanded it down and and was about prime.  This is a nice piece from that last running cadillac and has the built in baffle that many prefer. Price is $75 + s/h. I will be out of town this weekend but can hold it for you. If something you want to purchase shoot me an email to jasonedge@nc.rr.com.  I can send some pictures...it's bare metal right now but can prime probably tomorrow.

YEs, hold it for me,,  i am going to be traveling to MS over the next few days as well so right now there is no rush.  it just never occurred to me that the area that was braised or what ever that is, it wasmnt machined smooth but it was rough enough for him to feel the need to do something to it to smooth it out

Here is my question, and I think i know you explained it once but am asking again to refresh my memory..

can the rear oil pan gasket leak on either side of the flywheel cover or would it be side specific?  like i said, the open side does not have oil on it, just wondering if that would help in diagnosis. 

Kim, Sanding on oil pan completed this am and sent email with payment info. I sent 7 pictures but have inserted a couple here. Not sure who you are directing the question to or really understand the question? Oil coming out of the rear oil pan gasket would tend to fling toward the rotation of the flywheel ... not sure what is "open side"?

Here is a repeat of some info I sent via email:
See pictures at bottom for reference:

OK. So at rear of oil pan area you have from top to bottom: -> A. a rear main bearing cap.
-> What goes beneath it? –> B. the oil pan gasket.
-> What is beneath that? –> C. the metal edge of the vertical transmission inspection pan. 

So what happens if B: leak? –> the oil is going to go to the rear and behind the vertical inspection pan and leak out the bottom of the lower inspection pan. (see yellow arrows in 2nd picture)

So..what can you do to get a better view of what is going on? Remove both inspection pans, clean everything very good, run the engine to the point it would leak or starts leaking and pop under and inspect. If you can leave it running then better.  Oil at that point should be seen coming out of the rear oil pan gasket, hitting the drive plate and splattering everywhere at that point since the inspect pans are not there to hold the oil back and way from the engine.
That would be my suggestion at this point.
 
If the oil pan is compromised on the rear edge where the rear gasket is seals it against the block it should be addressed anyway and have a nice oil pan for you to take care of that problem.
 
Torus Vertical Inspection Pan:
 
Torus Vertical Inspection pan installed, lower pan removed, showing torus and drain plug:
Back of engine showing Hydra-Matic Driveplate for reference:

Finally got to MS and mych warmer temps

  Got cAr up to change pan.  Other than pulling the exhaust apart and bending it during removal of car off trailer went ok.  Its a trip it exhaustvshop now,

Anyway i hv attached picture of old pan were it attaches to rear of block with rhe braising that i refeered to earlier.  Its just a reference shot but thought i put out there. Will take car for ride maybe tomoro if rain holds off.

Its on!   Kinda hard to see the old pan imperfections.  Cnt belive the cheerry bomb thing hung one of the cross bars on trailer n bent exhaust,  wat a headache

I patched it up w a exhaust flexible duct work,  hi temp jb weld,  but uts gonna need to be fixed.  

If weather hold .  I will take for test ride tomoro

i know all are sick of reading about this,,but for the first time i saw oil come out,, i put on the new pan,  not without misery, but got it on. 

got it going,,, long story short,, leaking!

got back pulled bottom inspection pan.. and turn on, while engine was till hot from the 10 mile ride and just let it idle for a bout 15 minutes.  i looked under lot of lights and could see it dripping off that alignment nipple, at a pretty good rate.  so i got close as  could, with engine running and flywheel turning.. and it seems to be coming out at the contact point of the rubber gasket on the rear of the oil pan,,just left of the center nipple dripping down draining over, going to least resistance down the nipple, and what doesnt go down the nipple, slide down the silver piece or black, behind the vertical inspection plate onto the flywheel, making it somewhat damp,, what i did see on the enclosed side of the vehicle inspection plate was very little as i think it was just some through off on the spinning part.    it was basically exactly how Jason described a few post up,,, 

it was odd though as i Looked,, if you didnt look right away, the oil would slide of the front and the back of the inspection pan and basically dry, i guess because the heat had it so thin,  and that is why in prior efforts, i never would see much if very very little on the front or back of that vertical pan, but the horizontal pan would have oil.  being that the surfaces are almost slick clean from so many cleanings after removal.  live and learn i guess...

now,, i am just guessing this is now an application/installation of oil pan error...if indeed that i what it is,, its a correct and unaltered pan.  so it should go on wo problem, but i seem to have to do something 20 times to get it right,, 

i have used the right stuff permex on top and bottom of the gasket,,  sealing both sides. on the cork/felt gasket and on the rubber inserts on each end..

i dont really know what to do differently.  I am also guessing the old pan with its imperfections was not seating as well due to the imperfections,  i just never looked at it under the above outlined circumstances..

i am going to take to exhaust shop on monday,, get that done, get rid of that damn noisy cherry bomb thing and have a quiet something put on.. and repair existing pipe itself where i bent it getting it off the trailer.. what a e fing headache.. and, order another gasket for the pan. 

SOOOOOO,,, any tips, tricks, materials ideas on how to make a good connection back there,,

im all eyes and ears...

Yes,  the long alignment one that pokes through the pan. In center  in center.   

Well i dnt kno wat to do nxt.  I a. Going to chg the pan gasket, ine more time after exhayst gets fixed.  I had some access issues that may hv led to bad installation of gasket an pan.  

If there is no way to disecern between pan and rear seal leak,  wat else is there to do.

I feel pretty confident that the shop i took it too did it properly,  he comes well recommeded,

If after that,  im just gonna kerp a 5 quart of oil bottle in car and carry on.    

N

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