Thanks for all of the replies. I will address several.
I would state that the general consensus is that modiying the nut that holds fifth on a stock NV4500 will work for awhile depending on the useage but not for long term. As with everything, there are exceptions.
I put in a rebuild with a fully splined shaft roughly 100k ago. It has been flawless up until now. With a little searching, I learned that more than likely, mine has worn to the point that my fifth gear no longer engages and that more than likely I have metal filings/fragments in the oil.
I don't even think that I will open it up. I am pretty sure that it needs to come out and be gone over.
The NV4500 is a good design up to a point. The inherent vibration and torque of the Cummins test push it over it's limit. The reality is that this engine is a medium duty truck engine and is often modified (as mine is) to push out more than stock HP and pull more than anyone imagined way back when.
Air to shift a RR is not the big issue. Weight and the height of the trans are. If I had a shop and better welding skills, a bigger budget and more time, I might go for it.
Along with the trans, my South Bend clutch has the same 100k on it and while the clutch is still strong, my throw out bearing needs some attention. Might as well rebuild the clutch while in there.
Couple all of these things together and factor in my ride to work. This truck has been my daily driver, hauler and hot rod for a long time. Albeit, not cheaply at times. I think it is time to buy a beater for going to work and upgrade the truck to an FL70 Freightshaker or something similar to support my farm endeavors.
By the way, on my starter issue, I had replaced the brushes around 110k ago after it stuck and burned up my shutoff selenoid. I am going to check out the cables because that is a common issue but more than likely, it needs a complete rebuild.
All things considered, I think I am going to post the truck on Ebay as a parts rig.