99 problems and a Ford ain't one.

I am in agreement with the majority of people who have said that the fuel pressure is too high, you have said that the oil is not washed out with fuel, so that supports the theory that the gauge is nfg. It's very likely that the old cam left behind a lot of junk and it has scored the bearings in the entire engine. What caught my attention is the trunk mounted battery and my question is what gauge is the cable that you have used for the primary wiring. Anything less than a 2 gauge cable can cause serious voltage drop over the length of the wire. Also a really good solid ground is essential for all the electronics to function properly. I have seen the results of voltage drop on multiple systems, it ain't a good thing. I don't expect it is the answer to all of the problems that you need to correct, but it may be a start.
Old rule of thumb is 10 psi of oil pressure for every 1000 rpm is key for a long healthy life for an engine, especially an old performance engine. Lots of modern cars have significantly reduced their oil pressure to aid in fuel efficiency.
I am running 4 gauge for my cables. It is grounded at transmission bell housing. I think you are right that the bearings are trashed. I found a 69 383. Think I will just go that route. I am over this 340. I agree on the voltage drop too. Cranks great cold, but once it is warmed up it is very slow cranking.