Too old for computers and coolant sensors, but I've sort of solved the starting problem, it's half an easy fix and half a difficult fix. The timing chain is showing it's age and when the engine is hot 700CCA isn't enough to turn the bid ol'460 over. 930CCA is. That's the brute force fix, but the timing chain is one of the factors leading towards a rebuild. I know it's not the coil or the starter as both are new and the way the symptoms are (perfect start when cold, engine seems almost like there's a bind when it's hot, cool it down and start perfect again) really don't lead towards those. The odds of the started or coil always landing on the same bad spot are pretty slim.

Capital - I'm leaning towards the thermostat for the cooling issue, flow seems to be good for coolant, and I just flushed and changed the coolant and that seemed fine.

The bad new is that the oil pressure gauge is accurate. It's just going to need a rebuild soon. I'll drive it for a bit and solve all my problems with a total engine rebuild

Thanks to you who sent me to Mark at Michigan Off Road. He's actually closed down his shop, but was happy to provide some advice and steer more towards a shop for the soon to be done rebuild.