You may have put us onto something. With that vintage of tractor and sitting up, what you may have is a carbonized combustion chamber which results in gunked up rings among other things.
They make fuel and oil treatments to decarbonize engines. I know Marvel Mystery Oil, been around for 50+ years treats gas and diesel engines. You can use it in the oil and in the fuel. It's really not an oil, more of a solvent. Directions are on the container. Most all auto parts stores and WW has it. Follow directions on the container.
Get a case of oil and handful of filters. Be sure and use oil rated for C service, not just S. Look on the back of the container. C is rated for compression engines and S for spark. It may say something like C4/SJ. When the oil gets dirty, change it and the filter. Chevron Delo, Shell Rotella T are a couple of good ones. Keep the treatment up till you are convinced you are there or fighting a loosing battle.
Make getting it out and working good part of the process. Hook it up to an 8' disc harrow, or 2 bottom moldboard. Run it fast as is reasonable. A 6' shredder in high grass going at a good clip. You may resurrect this tractor with minumum effort.
I have a '63 2000 4 cyl diesel with 3500+ hours and it was doing a lot of smoking; not your problem but still solvent related. I used some Diesel conditioner made for cleaning up injectors and upper cylinders; bought on same isle as MMO. Used it for awhile and exhaust smokes very little now.
As stated, oil blowing out the engine is nothing but engine compression blowing around the rings and out any opening it can find.
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