Need some opinions on where to go from here...

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One thing I noted from your photos... looks like the block still has the dowel pin on the china wall for the OE intake end gaskets to locate. If that block was decked at some point it's possible the dowel holds the intake too high giving you sealing issues. Most people remove the dowel and make their own end gaskets with a thick 'ol bead of TheRightStuff. Probably not related to your problems but something to consider looking at during your re-assembly...
Yes, good catch. When I assembled the engine on the stand out of the car, there was actually a very small space between that dowel and bottom of the intake rail, so I just left it. The intake actually sealed up really well, front and back and on the gaskets.
My guess, either fuel pump ruptured the diaphram and filled the crankcase with fuel. Not sure how long it has been run, but that scenario kills bearings. Or the carb might be dumping raw fuel out of a booster and washed the rings. Making the marginal ring seal situation very problematic. Are all the valve tip heights equal?
I never even knew this fuel pump issue was a thing, but I will be checking it. I already have a plan for moving forward once the heads are out and engine is in.
Good catch. When I first got these heads, before I did anything with them, I ran a straight edge across the top of the valve tips, and all was well. This was important too for when I went to order the rocker geometry kit. My photo isn't the best and it may just appear that way, but only way to know is to check, so I will check it again when I get out there. The valve should be closed all the way, especially since I did a leakdown test without rocker gear and had nothing leaking past any of the valves, or leaks at all for that matter...but I will check this again. Thank you for pointing it out!
 
I ran an electric pump with a mechanical for years. Was always a concern for me, (increased the chances of it happening) I know someone who spun a rod bearing when a diaphragm failed.
 

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