Without being run too much, condensation forms and doesn't burn off when you run it 20 minutes here & there. Also, if the boot over the shift lever is cracked, rain water seeps in there.
IIRC there should be 3 plugs under the transmission. One should have a screen on it and that is where the pump suck the oil, and the other 2 are drain plugs. I forget exactly how much oil our 1855 took (Oliver version of your White) but I think it was around 8-9 gallons, so 2 pails would fill it for you. And as you have found, it's almost impossible to remove the filter without destroying it.
It uses the same filter as the hydraul shift. (Wix 53107, or NAPA 3107)
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Today's Featured Article - Hydraulics - Cylinder Anatomy - by Curtis von Fange. Let’s make one more addition to our series on hydraulics. I’ve noticed a few questions in the comment section that could pertain to hydraulic cylinders so I thought we could take a short look at this real workhorse of the circuit. Cylinders are the reason for the hydraulic circuit. They take the fluid power delivered from the pump and magically change it into mechanical power. There are many types of cylinders that one might run across on a farm scenario. Each one could take a chapter in
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