When you go to change the rear main make sure to have this list on hand:
Cummins rear main set (Mine had 230k and did not need a sleeve)
the two plugs that are above it in the photo to the upper left
the gasket behind the rear main housing
Tube of high quality silicone
***This is also a good opportunity to extend/replace the breathers for the transmission/transfer case to a higher location***
When I changed out my clutch and overhauled my NV4500, I also changed the rear main. I ordered all the parts before even pulling the transmission, as in the tractor dealership I work at, we have found that if a unit is due for a clutch, the rear main is another 20 minutes to change while in there. That was discovered after have a couple unit get clutches and then within 6-9 months they came back for an oil leak. Based on that experience I went into working on my own rig with the same logic: change what ever wearing parts you can while doing a job. I do not like doing a job twice because of either laziness, cheapness of lack of research.
But back to you: when you get to the seal, pull the housing it is in, change the seal on the bench and then reinstall the housing. This will allow the seal to self center on the crank as you carefully torque the housing back down.