I dont think I have ever seen a trans this dirty,lol. I would knock some of that grease and crud off of it first before cleaning the inside. There are 5 gaskets on this trans, the top loader, the front bearing retainer, which you cant get to unless you remove the trans. The rear bearing retainer, which you can replace if you remove the rear ujoint housing and u joint, this one is what is leaking by the looks of it. The PTO cover is the 4th gasket. The fifth is between the rear bearing retainer bell and the mounting retainer of the universal ball. There is a cork seal on the universal ball and slip joint bell flange at the rear of the ujoint as well as a small cork seal on the small end next to the torque tube. Knock some dirt off of it and it will come into focus better.
1953 Chevrolet 3100261 cu inch, sm420, 3.55 rear, torque tube still,omaha orange, still 6 volt, RPO green glass, side carrier spare, all done
In the DITY GalleryVideo of the 261 running1964 GMC 1000305 Big Block V6, sm420, the next cab off restoration