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Hi Don, if I replace the rings with DRY compression at 90 is boring and sleeving a high need?

Without seeing it, I can't say so you'll have to judge that by the condition. At the very least, you could try honing to see if the grooves are removed.

Don/Jason, Correct me if I'm wrong, but is breaking the glaze on the cylinder wall by honing it not a requirement to get the new rings to seat properly?? Chris

Ross, I missed a couple of your questions.

When the car overheated the oil light did not come on, my sender triggers at anything less than 15psi

On your recommendation to clean the engine with a wire wheel, are you suggesting to clean the area not colored red in the attached images? I ask because I thought I had to be gentle with those areas.

I'm surprised I can re-use the gasket

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Jason, you should use a new head gasket for the final reassembly. I think Ross is suggesting re-using your old one just get to the bottom of your noise source. Chris

Thanks Chris, that makes much more sense... Thanks!

Clean up the areas you marked and the matching areas inside the head. Clean the tops of the pistons too, of course, but be careful of stray wires from the wire brush. I've seen engines where a strand had stuck under a valve and caused it to burn to the point that it had to be replaced. Maybe use a shop-vac while brushing/scraping to minimize any wires or bits of carbon from getting stuck anywhere and clean and vacuum thoroughly again before cranking the next piston up to the top.

Yes, do the whole top of the engine and while you are at it, clean up your studs with a flick of the wrist.

The piston rings wear thin --especially in long stroke engines and start to rattle up and down in the groove. After a while they break from flexing in trying to seal up a heavily tapered cylinder The individual pieces really rattle in the groove and sometime wear a path right up through the top of the piston. Chances are your lands on #2 are already toast.

See if you can borrow some tools to measure your bores top and bottom.

Don: Thank you Sir! I will be sure to do plenty of vacuuming

Ross: Thanks and will do.

I assume removing the water pump is needed to fully clean my water jackets. Is there any way to test that the pump and impeller are functioning properly? I don't see anything about testing to see of the impeller is functioning

Seems like it would be foolish to have the vehicle as broken down as it soon will be and not remove and clean the water distribution tube.

In the photo of cyl #2 (marked in red) , a small piece of the piston is missing, or burned away. With the exception of cyl #5, all are using oil. The pitting in the cylinders is the result of long term storage without lubricating (aka pickling). When rust forms in the bore, and the engine is rotated, the rings will scrape the oxidation loose , where it will lodge between the piston ring and the ring land. When the piston changes direction, it rocks. The particles that have accumulated will cause the ring to stick, resulting in lost cylinder sealing. The 2nd ring's primary function is oil control. If the cylinder is worn,or out of round, the ring cannot seal and the engine will use oil. Oil in the cylinder will cause detonation. Detonation burns pistons, breaks rings etc.

Assuming that your engine has mechanical tappets, roll the engine over and measure valve lash. Measure the intake lash when the exhaust valve starts to open, and the exhaust lash when the intake valve starts to close. Record the results. Examine the valve springs, observe the motion of the valve.
While the valve is open, look for cracks in the seat area.

Good luck.