Gizmo,
FWIW, here is my .02 to the questions I believe you had. For my opinions, I have assumed that you are not used to driving large vehicles, especially on a regular basis and that you are not a diehard mechanic that likes to plink and tweak your vehicles for performance.
1- You want a SRW. As a daily driver a DRW can be a pain, especially for one that is not used to driving such a vehicle on a regular basis. Yes this could limit some 5th wheels, but you?re at pretty small trailer now and I can't see you having to the max size available trailer to be happy. There is some increased DRW costs as mentioned, but they are probably minimal in the scheme of things. DRW is worse in snow too. (if you plan to leave AZ)
2- The Diesel Exhaust Fluid (DEF) additive is a VERY negligible cost. You put in a few gallons every 5-8K.
3- The power and reliability of the newer Diesels are amazing. Some here have alluded to the Power, mileage, and reliability of their ?favorite? older trucks. I don?t see you as one that wants to always be researching, modifying, and plinking to max your trucks ability. Not to mention in older trucks, like it or not, start to require maintenance and on occasion have an issue (Alternators, starters, bearings galore, etc?). That is not cheap and can ruin trips, especially if you are not a mechanic and/or prepared.
#3 is what made me upgrade from my ?97 PSD to a ?11 PSD. For me when I have a weekend or family in for a fishing trip, etc., I couldn?t afford a hick-up. Reliability is important to me (Time=Money) Yes anything, new or old, can have an issue or breakdown, but as a general rule of thumb IMO the newer is more reliable.