Pulled the Mess that was my Timing Chain....

How many miles on the engine? And what other issues are there so far? I am not sure what issues you refer to with the 'top end'??? The chain and cam are part of the 'bottom end'. The '100' part of 100-115 psi is a bit on the low side. Common things I would be looking for are worn valve guides and worn rings/pistons.

If you replace the engine, don't toss it; there are some /6 guys up in the PNW who I imagine would take it. (Which is why you should post some on www.slantsix.org; several are there.) As for putting in another engine, if it is known good, that is one thing, but if not, it can be the same thing all over. I guess my main concern what to do with the groove behind the cam sprocket (assuming that is worn). Putting in another block is the easiest.

If 'twer me, I'd pull and rebuild at this point' specially if you are planning other mods. But, I also have not seen the engine or driven it so that makes my input sort of a knee-jerk reaction based in limited info. And, I have done a goodly number of engines so it is not daunting, and I don't mind spending the $$ on modest rebuilds because that is entertainment for me. Others won't view things the same way. You at least have plenty of support for this at the shop and with your dad, however you go.