Hello Bob, ACMOC tries to help EVERYONE. We don't belittle ANYONE. If you think you are more knowledgeable and mechanically inclined than others, congratulations! Just keep it to yourself! 
In my personal experience, someone who enjoys putting others down, suffers from low self esteem.
Craig

Update.
Upon further inspection and checking the fluid levels with more precision I determined that it is likely the transmission that is losing its fluid. The trans was several gallons low but the winch was pretty full yet.
New question does the trans also have a pto shaft seal on its side of things?
I can’t picture how that looks back there and does the pto shaft run through the wet compartment on the trans where it could be losing fluid if a seal was going?

The winch looked good inside and functioned fine today.

The Winch bolts up to the transmission case with a gasket, the PTO shaft runs past the Crown Wheel, that whole area is wet.

Wombat

The seal on the pto shaft is a double lip seal but it keeps the winch oil and the transmission oil separate.
This is why we need the rest of the story so we can make a reasonable WAG.
The flange on the winch has an O-ring seal.
It is supposed to keep the transmission oil in the tractor.
Bob

Item 10 in the PTO shaft diagram is the o-ring seal between the tractor case and the bearing carrier. If that o-ring is leaking you can lose transmission oil. There is no winch mounting gasket as there is actually a space between the winch and the transmission case. Only the mounting bolt bosses actually touch the tractor main case.

Alright thanks guys for the advice.

I’m going to wait a few days until it dries up around here then use the machine again.
I’ll take a few better photos of where all the fluid is dripping out in the dirt after it warms up.

Thanks

Take the covers off under the fuel tank before you run your tractor so you can watch the top of the tub, there are transmission oil tubes on top.
Hopefully it is a o-ring on a tube.
Bob

That is good advice. Want to look for the leak source (if you can see it) not pictures of leakage point of discharge.

I have removed the back cover under the fuel cell as the first line of inspection.
I also replaced the suction and pressure hoses to the winch about a year ago so they are good (forgot I did that)
Everything is dry on top,
It just seems like it’s coming from where the winch mates to the tractor.
I’ll wash it up and see what it looks like then.

Correct me if I’m wrong but there should be no pressure on that PTO shaft seal on either side of it right?
Also it should be above the fluid level for both sumps correct?