Receiving some much-appreciated help from my friend allowed me to remove the old head without suffering loss of life or lumbar. Check out this decapitated 258:
All in all, we're not looking like we're too bad off. There's some slight marring of some of the cylinder walls, but nothing worrisome. The biggest problem that we saw was the stop leak used by the previous owner appears to have been used less as an aid to address a leaking heater core, and more of a fix for a leaking head gasket.
The pushrod chamber walls are lined with crusty garbage that the stop leak bound to when entering this area through the gaps where the gasket wasn't sealing. I'm optimistic and think that this is localized to that part of the block. I've changed the oil in this a few times over the years, and while the first change was a little gross, the later changes were fairly clean. We'll see after the pan comes off in the next day or two. Right now I'm building an equivalent of another specialty tool:
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