Your experience is very common. There is a thread about it here virtually every other week. Though having a good gear shift boot is good, don't expect a boot or a roof to keep the water out. All gear cases are vented to keep the bearings from being ruined by the constant expansion and contraction of the air in the case. If you work your tractor and get the cases hot, as it cools some air will be drawn in. If the humidity is high, there will be moisture being drawn in also, If it gets cold that night and the housing temp gets below the dew point, suddenly there will be condensation on the inside. Have you ever seen condensation on a heavy piece of cast iron? or on concrete. The same can happen in your engine crankcase, except you will get moisture as a product of combustion in it every time that you start it. Normally a car or truck engine heats up enough in just a few minutes to drive the moisture off, but tractors often have a more massive motor and need to actually do some work for a little while to drive the moisture off. Starting a small tractor engine and letting it run for five minutes is as bad as a two mile twice a day commute is for a car.
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