Dad was plagued with leaking on his Fordamatic in his 59 Villager.
It was hooked to a FE332. All the cases he found had the same problem.
Most were cracked at the shift bosses and leaked there.
He had some success by cleaning with acetone, and using JBweld.
He ended up putting a Cruise-o-matic in out of a 65 390 Galaxie.
You couldn't tell it unless you crawled under it, and of course listened to it start. That was an added benefit, later model starter that would kick off every time without the bendix whizzin. He also had to modify the driveshaft length. The shift linkage worked fine. If you just put it in "D" it would start off in 2nd and shift once, but if you pulled it on down into L it would start off in 1st. I just put a cable actuated kickdown on it because the cruise linkage was reverse of the Ford a Matic, and a lot of the time they kickdown when I don't want them to.
I know he was better pleased with the Cruise-o-Matic, and was much better on the road.