I think Dave you need to look at this in the very very long term.
You are probably going to be using this truck for a while now that you have it. Lets face it the factory stuff isn't that nice as far as HVAC or ergonomics or anything like that.
So if the goal is a cummins well then there are certain things ya gotta do.
The vintage air system is the best way to do it. And is a far superior system to the stock one. That gets the AC stuff out of the way and makes for a pretty engine bay.
A VE pump cummins as has been said is not a bad engine at all. And lets face it Dave you are not know for good self control when it comes to engines.
So if the eventual goal is a cummins ( a rebuilt 454 would be cool swapped into the jeepster

). Then start making plans with that goal in mind.
With my dually my plan is a cummins, eventually. I am not getting rid of this truck though at all, and I like you won't really be daily driving it. But it sure is nice to set the cruise at hwy speeds and leave it there. Its also nice to have something else to drive when whatever is down for work or something. The cummins makes it even possible for me to think about daily driving it instead of with the gas motor when it would be a oh crap I need to drive the dually.
So while the power with the cummins is so nice I am planning the swap to make my dually more daily driver friendly.
The 454 I am building now will find its way into something or other.
So I think if the long term goal is the cummins then there are several things you need to do first, then worry about finding one.
Also I am very much looking forward to seeing how much overboard you go with this truck
