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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