Pearson 365 and 367

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I'm not affiliated with this boat but I know it's being sold by the widow. I also have a Pilothouse and we were docked together a few years ago. It'.s currently on the hard in Bayfield Wisconsin

I still have the Stearns Dynafurl from 1980. I purchased new bearings from Rig-rite for some outrageous sum and copied the numbers. Years later I replaced them with bearings ordered from a local outlet for a much lower reasonable sum. I also made sure to pack them in a lot of grease and then siliconed the threads on the end caps. Eighteen years later they spin like new.

You could reinforce the panel from behind, maybe put a SS fender washer under the stop button for cosmetics.
You could replace the switches with new caps.
Switch Link

That looks like the right cooler. I need to get to the boat to check the hose placement, but I do know one comes out of the top of the case. I believe that is where the oil flows out and the other is the return. The water should flow in the opposite direction through the cooler.

#58 bulb in my original anchor light. I decided to install an automatic led light when the mast was out a few years ago but left the original so I could delay repairs if not convenient. Belt and suspenders. 

Here is a good article about replacing the damper plate on a Morgan OI.

https://goodoldboat.com/pdfs/GOB78_DamperPlate.pdf

Welcome! I'm guessing you have a Paragon transmission. They do not have a detent for reverse and you need to hold it in the reverse position. It doesn't have anything to do with the v-drive. Here is some information from an earlier post:
https://pearson365.com/forum/index.php?topic=2105.msg10898#msg10898

I doubt it would last through the hurricane. Usually you want to reduce windage and remove sails and canvas.

I'm inclined to agree that it at least needs retorquing. It may be too late, and the head gasket may need replacing. It's likely the combustion pressure is leaking into an oil passage causing high crankcase pressure.

Sen-Dure is another option, I had looked at them years ago, but I was able to get a repair at a radiator shop.

Well, I did find these posts;

https://pearson365.com/forum/index.php?topic=900.msg4341#msg4341

https://pearson365.com/forum/index.php?topic=739.msg3410#msg3410

Here is a video a friend made of his 367. When we first met he was traveling with a 365 ketch and I have the pilothouse so all three versions were together.
https://www.youtube.com/watch?v=EwcJSGgPLgE

I was still working full time but thought doing boat canvas work would be a nice sideline and make foR a nice retirement business. Of course everyone wants something during the boating season! I always felt uncomfortable at the marina, either someone wanted to see about a new project or questions when an order will be done as I try to relax. I finally quit. I still make stuff for myself and will gladly stitch up a seam or two for a friend but thats all. I was in Buffalo a couple years ago while bringing a friends boat to Superior WI and stopped at your store, sorry I didn't get to meet you but your daughter sold us a few things. We spent some time at RCR and Andy Lopez told me he had owned a 365. I hope you get some sailing in and everything works! It's funny that even though everything is working when I put the boat away in the fall ther is always something that gives me trouble it the spring. As far as lists go, it seems whenever I cross something off I add another item or two.

I wouldn't go below the mark, but if you are down 3cups I'd wait to see if it continued to 4. While I have a BMC 1.8 my dipstick reads almost 1 quart difference from one side to the other because of the angle. Did you check ring gaps when assembling? They should also be 120° apart. You should run it fairly hard to break it in, 2300 is not too high.

That sounds like you are proped about right. If you are overloading you should see a lot of black diesel soot on the boat, but it shouldn't be burning lube oil. Are you sure of your dipstick fill level? You say you burned 3 cups of oil, so I wonder will it hold at that level or will it continue?