You need to use more piston ring end gap on the top rings with KB hyperutectic pistons because the top ring groove is closer to the top of the piston so they get more heat and expand more. Follow the recommendations supplied with the pistons not the rings.
Don't have valve seat inserts fitted to the intakes if you do you won't be able to fit them to the exhaust which you should do. Have them crack tested before you spend any money on them.
There's nothing wrong with the original points distributor set it up correctly, don't leave the ignition on with the engine not running and it will be good. These cars don't do lots of mileage and points aren't that difficult to replace anyway.
I do remember reading about a special race engine that needed the oil and coolant to be pre heated before start up they said if it was started with cold fluids it would cause engine damage very interesting.
Cold oil is thicker then hot oil once the oil is up to operating temperature the pressure will be a bit less this is normal for any engine. Old engine builder rule is you want 10 psi per 1000rpm for so yours is good for around 5000rpm sounds good to me.
I had the same thing with an Optima yellow top went to tighten the positive terminal clamp and the post came out of the battery I think they went bad when they started making them in Mexico. Had a US made red top lasted over 10 years and wasn't even well looked after.
That blue looks like a rust proof coating if it was blue from heat definitely wouldn't come off easy. There's no blue where the bearing sits which would have been ground zero for the heat. If the bearing is a little loose on there you can stake it a few times with a centre punch to reduce...