Either way you go, there are upgrades out there.
With the Cummins, you can fire ring the heads and add head studs which will hold up to a lot of boost. There are several custom tuners out there that can write tunes for the Cummins.
I am guessing that you are wanting to upgrade to a dually for towing 5th wheel trailers and heavy tongue pulls. Tune for Tune, either is acceptable. The new Cummins sucks diesel just as bad or worse than the duramax's before the Urea system. The extra shot of diesel after combustion is killer on both fuel economy and on oil changes. IIRC the Dmax and Pstroke were both going about 7,500 miles before excessive fuel contamination into the oil. Since there are less cylinders, the fuel contamination on the newer dodges may not be an issue.
If you are looking at the 24v 5.9's then, go for it. If the 04 dmax is paid off, keep driving that one as well. Just remember, one that is paid off makes money every month. That is why I keep driving mine. I could afford a new one and would really like to have a new Denali, but why when what I have is paid off.
Look around the junk yards, You can probably find a wrecked dually Dmax (or a gasser) cheap and spend a couple of days swapping parts. The bed should be a drop on item, and the rear axle assembly I don't know about. Probably just a leaf swap and axle end assemblies with hats. If you find a dually on the yard somewhere, you can probably make a swap for some of your stuff, then have the axle rebuilt so that it will be a quick swap.
If everything is ready, meaning that the axle is ready to drop in, and the bed is ready to go on already painted, then I can see where 2 semi skilled mechanics could make the swap in 1 day or less. With the use of a lift, 1 person could probably make the swap in 6 hrs or less.
Hate to loose anyone to another brand, but if making the swap at least it is not to a Ford. You know what you need. Also, having a fleet of the same motors makes it easier to work on one when they do break down. Regular maintenance parts are easier to stock, and you do not need to be extremely specific when asking help to grab a filter or something for you off the shelf.
That is my $0.02 on it. Whatever you do, don't stop visiting the board just because you no longer drive a Dmax.