There are orings at the bottom of the cylinder liners that can leak.
And there were problems with the block cracking between the webs at the bottom of the cylinders. I'm about convinced this is caused from freezing, not the engine design fault.
Oil in the coolant though is strange. The only way oil can get in the coolant would be a severely blown head gasket and running it a long time. There would be other symptoms, like misfiring, steam out the exhaust, blowing coolant out the radiator, and mystery coolant loss (which you do have). There is an oil passage through the head gasket, but it is very low volume, metered flow, at very low pressure. Possible but not likely to be the source.
You can try filling the radiator, pulling the plugs and letting it sit overnight. Spin it through and see if coolant blows out any cylinders. Best to apply low pressure to the radiator, but I doubt you have the tools to do that and it may not hold pressure or could start the radiator leaking.
Another test is a combustion gas detector. I suggest you get the kit and run this test. It will tell if the problem is a head gasket, or cracked head (not a common problem).
You can (and should) also pull the oil pan and look up at the bottom of the cylinder liners for leaks, and look at the block for cracks between the cylinder bores. Do this before taking the head off.
If all looks good below, and you do take the head off, do not turn the engine while the head is off until you clamp the cylinder liners down with bolts and washers. The liners just sit in the block, any movement will cause them to start leaking around the orings, which means they have to come out, be thoroughly cleaned and reseated with new orings. (Not a bad idea to do that anyway at it's age.)
This is going to require timely attention. Letting it sit with coolant in the oil and cylinders will quickly damage the engine. Having a shop manual in hand before starting this is a must! It will more than pay for itself in mistakes not made!
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Today's Featured Article - Tuning-Up Your Tractor: Plugs & Compression Testing - by Curtis Von Fange. The engine seems to run rough. In the exhaust you can hear an occasion 'poofing' sound like somethings not firing on all cylinders. Under loaded conditions the tractor seems to lack power and it belches black smoke out of the exhaust. For some reason it just doesn't want to start up without cranking and cranking the starter. All these conditions can be signals that your unit is in need of a tune up. Ok, so what is involved in a tune up? You say, swap plugs and file the points....now tha
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