Build Off to a Good Start. My '74 40 Series

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if the engine is cranked with the starter would that also push oil up through the oil passages?
Yes, though it can take a minute for the oil to get up to the top...
 
I was thinking of one more option to check for oil flow here.
It's good practice to run the starter motor without starting the engine on a motor that's sat for a while.
 
I also ran the drill at this point and didnt see any oil. Next I was going to remove the oil filter and run the oil pump again but had to step away for a bit.

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In your second picture, the one with the engine block, do you see the one bolt in your side cover with the spacer behind the head of the bolt? It’s right after the #4 cylinder. There’s a threaded hole for a head bolt in the block directly behind it. And a small hole in the block a little further in. THOSE TWO THINGS are supposed to be connected by a teardrop-shaped hole in the head gasket.

You can see the impression of the teardrop passageway left by the old head gasket on your cylinder head.

Pretty sure I have a ‘74 head gasket on the shelf.😉
 
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Thank you Mark, I see. What you're saying is this would be blocking the pathway and the proper head gasket to use would have had a teardrop shape void, similar to the gasket Pighead had shown previously? But I should get oil up through the headbolt hole now if I run the oil pump with the drill, maybe I didn't run it long enough.

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Is that an F head gasket then?
Well, can’t say for sure. If we could see the WHOLE gasket, we’d know if it was just installed backwards (teardrop between 2&3) or an F gasket (no teardrop)
 
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I'm curious, would it damage anything if I left the oil filter off and blew compressed air backwards from the port on the block?

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I would be concerned if you could blow through the filter ‘out’, as those are the passages to the bearings, and they should be tight, so the oil goes where it needs to go. IOW, if it’s easy, the bearings are failing.
 
Could the blockage be just in the filter housing? That seems like an easy one to check off the list. Good to know the pump works.
 
I pulled the filter housing today and found a couple big globs silicone. I scraped all of that off and tried to shoot compressed air through what would be the filter out. Initially it was very restricted but blew something out and was able to push air through and could hear it through the block. Thinking I might have cleared whatever was restricting it, I put the filter and housing back on and ran the oil pump again to have it pressure up and not pump oil. Im fearing that the silicone might have found its way through, plugging/restricting the oil passageway through the block.

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Uh oh. How do you know it's not pumping oil and can you shoot air back the other way?
 
Uh oh. How do you know it's not pumping oil and can you shoot air back the other way?
I ran the drill at a little more than half speed, turning the oil pump. No oil flow through the block and I felt and could hear something pressure back up. When I hooked my air chuck up to the top port I could blow air through and heard air flow, but I could not get anything blowing backwards from this port back toward the filter.

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