I HAVE A 4520 power reverser 4X4 with FEL and so far this seal has been replaced 3 times once under warranty. and is again leaking about 3 gallons a week .
Reading the repair Manuel there is pictures of the stands needed to hold rear of engine and clutch housing. Would think that your 4400 might be about the same.
before separating underneath on front drive shaft remove the water hose clamp and slide the dual pipe toward the front . then separate the shaft first removing the small pin to slide the coupling to transmission housing. now can see where the oil is coming from
Drain hydraulic oil. mine has 10 gallons I use a 15 gallon plastic barrow laid on side so bung is on top side. and funnel into the opening . then drain.
remove the hanger for FEL and attach the stands
looking at filter and pipe to return into the transmission remove bolts holding the filter bracket to transmission.
The repair book says to remove the housing input shift shafts not all need to be removed. the one that is for engaging the 4 whl. drive needs to be removed but the shaft retainer doesn't.
also the Seat needs removing (standred John Deere feature) bolts for the pedals and that retain the platform book says remove the fuel tank and console not really needed unless you like a bunch of extra work. Have a helper help to lift and remove . blocking the rear of tractor at hydraulic transmission and prevent tires from rolling remove the large bolts that couples the housing to transmission Find two 12 " long bolts to insert into holes bolts are removed .
when checking and rechecking all holding is free slowly separate the housing. sliding on the 12" bolts . until can see into the housing release the keeper holding the seal in housing. then using a deep socket the size of the seal . tap and push into the housing.
New seal wash with Hydraulic oil and being sure inserting the same as removed tap into place then reassemble.
My feeling is some engineering type could have made to install with out all the labor. remember when seals were installed and a metal holding plate and 2 small screws held in place.
It reads and sounds like a bunch of work but think of 2 at 85 to 115 per hour each including coffee breaks also gets expensive for a 5 buck seal.
ken