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Yes, my '93 Merc has plain copper wiring, but my '77 Merc had tinned marine wiring, like the OPs motor came with.

Gee, it is very cute recommending waxing. I waxed my boat once in the 80s. The wax was gone in our saltwater, in minutes. Maybe in lakes it makes sense, but the salt stuff strips it, in my experience.

My gas gauge pegs on empty with 1/2 tank. I replaced the connectors on the sender and the entire ground wire and connectors. No change. I think the gauge is wired properly. The sender wire could be making a bad connection. Would that cause a lower then empty indication? Bad sender? Stuck...

Your motor would originally have marine tinned wires. Those do not look like those to me. Marine tinned wires are thinner and tined, vs regular copper wire..

Gee, If you are going to swap engines, can't you pull the oil pan on the leaking engine after it is out and replace the seal? Just a guess.

Gee, stick with a 90s or 2K 2 cycle OB, before the sophisticated electronics, fuel injection, direct injection etc. They are simple and perfected. My '98 Johnny 60* V6 is the pinnacle of 2 cycle multi cylinder engines IMHO. It has loop injection, 6 carbs or 3 triple throat carbs, depending...

Marykate on and off is two kinds of acid and acetone. It cleans most stains, but wear gloves and protect the galv trailer parts.

Plug wires on the correct spark plugs? Firing order is usually 1-2-3-4-5-6 on those 60* V6 engines.

It is doubtful that Crowley remans the blocks. It is likely some local shop that they buy from. I bought a Merc IL6 reman block from a rebuilder associated with iBoats.. It was fine, although it did not have the power of a new block. The price was right, I thought.

There are rebuilders of powerheads. iBoats has (or had) some sources. They ship a reman powerhead to you. You strip your block, transfer parts to the reman block, and ship your's back. Of course that gives you the same engine.

Lowering the prop pitch 2" gives about 400 RPM gain. Your boat may vary, but that is the rule of thumb.

Those will not be good ski boats, as they will put out a large wake. They will be good family runabouts.

Dedicated ski boats are best for serious skiing. They have direct drive or Vee drive with large inboard motors. They are geared down to skiing speed at WOT, giving great acceleration. For the rest of us mortals a recreational boat is best. If the kids want to ski, and plan to ski well...

Gee, doesn't a .015 bore require a new OS piston? Did he bore it or just measure it? The cylinders get out of round. Did he see that?

Terminal board? Gee how about marine adhesive shrink tube bullet connectors?

A stern drive is not usually a good choice or a ski boat. They are 1100 pounds or so, causing the boat to put out a larger wake. An OB will be less than half that weight, have plenty of power and produce a smaller wake. Anyone who cuts across the wake on skis will appreciate the smaller wake.

I think you want an OB powered boat 18' or under, with a 125HP or larger motor. You want a boat that puts out a minimum wake, so a flatter stern area is better for that. I would not get hung up about the amount of wood in the boat. It is more about condition and design. Not all boats...

I expect all you can do is clean up the contacts and see if that helps. Voltmeters like clocks need to be accurate and reliable. Your voltmeter is likely reliable, so you can figure out how low it reads and add that voltage on in your mind.

The service manual for my motor says grease on the orings, silicone around the water ports, when installing the cylinder head.

Compression leaking to the water jacket will cause overheat. You might check the head for warpage as well.