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 - Recollections of a John Deere GP - by Charlie Cook. I grew up on my dad's 280 acre general farm in Western Michigan. Dad's only tractor when I was very young was the old GP. My first recollection of this tractor was when dad allowed my brother and myself to ride on the tractor with him driving. One of us would sit on the left fender (away from the clutch) and other would sit on the gas tank and hold onto the crankcase breather pipe.
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