The plug you are pointing at, I the level plug. Fill plug in on top, near the gear shift. I've attached an old Lube Chart, from an old Gulf Oil catalog of multiple tractor lube charts I have. Shows all the lube points, and capacities.
If it has set outside, more than likely you have what looks like a milkshake inside the trans./diffy. Drain out that lower rear plug. Fill with a couple gallons of cheap Auto trans fluid ( Walmart brand is fine) A couple gallons of diesel fuel, and a quart of rubbing alcohol. Drive it around for 15-20 minutes, then drain completely. The ATF is high detergent, and will clean things up. Diesel fuel will wash it down. The alcohol will absorb any water/moisture, and bring it out with it. Another TBN member Soundguy, spoke of adding the alcohol years ago to the first two items I always used anyway to flush them out. Works great..!! Then refill, until it comes out the check plug. Capacities are listed at the bottom of the lube chart I attached.
*** It does look like the pinion shaft gear seal(s) are leaking, behind the brakes. I'm not sure at what point in time you plan to replace them, but, do be aware, you need to pull the transmission top cover, then unbolt the bull gear from the axle, to get the pinion shaft bearing cage out, to replace the seal. There is a relief cast into the bearing cage, that the bull gear goes through, to mate up with the pinion shaft. I've attached a picture below from Wenger's parts, to show this. If you pull the pinion shaft case, and not remove the bull gear, you'll break the cage. BTDT... One of the items they failed to mention in the I&T manual, in the disassembly instructions, for replacing the seal. Although it is mentioned in another section, a few pages further back in the manual.

Just wanted you to be forewarned, if you decide to do that job soon.***
Hope this helps....
(Edit) Forgot to mention, when you open the lube chart, you can save that image to a file on your 'puter. You can also print it off, and it will print out a full sized print, and save it, if you have a loose leaf notebook, if you have other manuals for it..
https://www.wengers.com/parts/media...8eab33525d08d6e5fb8d27136e95/p/0/p0001085.jpg
