Morning,
Spent 7 years in the transmission business and your question is more complicated than you think. You say you have a TH 400 with OD. Are you sure? Not a 700R4? You happen to have a picture of the pan of the trans? What year is it?
Let me answer the repair in short, the rear housing has a seal yes, but inside the housing is a bushing the rides the rear yoke. Usually when the seal leaks its due to wear on the bushing or yoke.
Back in the day, that repair was, remove driveshaft, inspect yoke, remove rear housing inspect bushing, and repair accordingly. If you can double check your trans type that would be the first place to start. Maybe it is a 400 but maybe it has a gear vendors OD unit on?
Other things you mentioned, was that when its cold it would not go into gear. This is a issue. If you low on fluid yes, it will hesitate going into gear because there is not enough fluid to build pressure to engage the clutch units. But if it is full, then that means the internal seals in the clutch units are hard and need to heat up to expand to allow pressure to build..
So in short, without seeing a picture of the trans and driveshaft it's hard to answer some of your questions about rear seal.
Living Our Dream
MTHRSHP - 2006 KSDP 3912
Cummins 350ISL...Spartan Chassis
ESC POD - 2019 Ford Ranger XLT FX4
Zippy Scoot- 2018 Honda PCX 150 on an Overbilt Lift
Shredder at the Rainbow Bridge - You Will Always Be With Us