you have some work ahead of you by the looks of it

Those iron heads are a dime a dozen , I'd start with another set, what part number heads do you have ?

Hey John how are you? Haven't conversed in a long time.

Welp, the horse has left the barn on this. I took everything into the machine shop, an old school mopar-friendly place, and the block needs bored and instead of putting money into iron heads decided to go with some Eddy E-Street heads and be done with it. Crank needs turned, the bearings were well on their way to being toast. So tearing it all down was a good idea. Was an incredibly filthy engine.

I'm doing ok , finally getting back to start working on all my dormant projects and to thin down my junk collection after having to move it all out of my basement after the town sewer backed up into it ...ugh .

That was probably the best idea to go with the e streets, rebuilding old iron heads isn't cheap , money well spent . Pay attention to the pistons you buy , off the shelf for stock stroke 400 choice isn't that great, you might have to get something from someone like Diamond? a possibility also is to look at replacement 440 pistons. There is a smogger piston that is is in the 1.9 CH range that will get you close to zero deck , you might just need to add some small valve reliefs depending on the size cam you chose.

Actually an easy fix. Hardest part is locating where the hole should be. Have it drilled for a 7/16"-14 thread then tap thds in, get a bolt or some all thread drill the end for 1/4"-20 thread. Cut the threaded end off to length needed to be flush or below surface. screw in a 1/4" bolt with a jam nut on it using red lock-tite on the 7/16 threads. Walla done. Just make sure the insert is flush, maybe file it flush.

The ship has sailed, I bought E-street aluminum heads. My heads were toast. Just got everything back from the machine shop. .030 over and .010/.010 on the crank. Time to start putting it back together.