Can't Measure MF 261 Transmission Oil Level.

I recently bought a 1994 MF 261. Before using, I changed all oils and filters. The problem I have is I can't read the level of oil in the transmission. No matter how many times I clean the dipstick or how long I let the tractor sit, the dipstick still comes out covered in oil. I know it's not overfull. In fact, based on what I drained, what the manual says, and what I put back in, I should still be 1 - 2 gallons short. Can I tell the oil level at the fill point? If so, how? Any ideas you have on getting the dipstick to work would be appreciated.
 
Does it need to run to fill some of the cavities in the transmission? I have had things go home that here ran for a couple days testing and running down the road looked fine but tip them going on a trailer or operate the right valve that I hadn’t yet and they need a gallon or even 2 added. Or some things don’t drain all the way perhaps you have an oil cooler or steering valves that weren’t quite empty. We had a 275 Massey at work that would get overfilled from time to time but it was mostly the loader hydraulics which I think on that were off their own pump the reservoir was in the frame of the loader
 
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Does it need to run to fill some of the cavities in the transmission? I have had things go home that here ran for a couple days testing and running down the road looked fine but tip them going on a trailer or operate the right valve that I hadn’t yet and they need a gallon or even 2 added. Or some things don’t drain all the way perhaps you have an oil cooler or steering valves that weren’t quite empty. We had a 275 Massey at work that would get overfilled from time to time but it was mostly the loader hydraulics which I think on that were off their own pump the reservoir was in the frame of the loader
I hauled it on a trailer 150 miles and mowed with it for a half day. I also operated the front end loader, and the mower is attached to the 3-point hitch. The loader acted like I was low on oil, but I can't tell. Everytime I check the dipstick it comes out completely covered in oil. Surely I am not the only owner to have this problem. Help!!
 
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