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Could I have run the motor too lean or rich and possibly burned a valve?
Would that cause the over heating and high oil pressure? Would I able to tell anything from cranking the motor with the valve covers off?
but the nagging question is why would it run fine and all of a sudden run poorly?

Mike I feel bad that I prompted you to buy a tester & do all that for nothing. Too lean could have burned a valve but the compression test would have caught it & cranking it w the valve covers off your good reading eliminated that also & yeah to run fine then act up sure got me to thinking (erroneously) the worst, that it was a head gasket. You're vac lines are correct. You might take a $1.25 can of starting fluid & spray around all 4 sides of the intake while it's idling, spray around the carb base & check that the carb base bolts & the little screws in the carb body, that one isn't loose & what is your timing at idle now.

live every 24 hour block of time like it's your last day on earth