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Usually maybe no, but if his timing is late it could.Nope. It won't get hot enough to burn the oil off of the block.
How would I go about verifying the timing? I know it could probably be tweaked a little one way or another. How would one change the position of the advance unit and how would that help? I’m sure if it advances it to far or not enough it’ll run but just really bad right? How does the vacuum advance work?Consider the amount of surface area of the exhaust tubes radiating heat, and that says yes, you will get more heat to exposed surfaces.
Definitely replace the valve cover gaskets, use good rubber ones since cork will dry out and fail.
Plus the cork soaks up oil, and eventually some can find its way past the gaskets.
Also, verify your ignition timing (as I noticed the position of the advance unit) if the timing is running late, that causes more heat plus reduced fuel economy and loss of performance.
I've learned from experience if it's 180 put, the misfiring 1 or 2 cylinders, can lock an engine up for a split second and completely stop the starter. That's all I can think of. .I was also curious as to why the engine hydrolocked from installing headers and dealing with plug wires and firing order, but weird things do happen.
I want to see him get through the engine running on all 8 correctly, then if need be we can hopefully walk him through any further diagnosis if needed.