Best of all generations

A 1st or 2nd gen 12 valve won't do you wrong.
See I told you you'd get some biased answers. 
Everyone here knows the'03s and early 04's are the cat's behind. All the benefits of the third gen re-design in a super reliable package with no requirement for a CAT or EGR. Plenty of upgrades out there for anything you want to upgrade.
Of course, any of them should do what you want, these are tough trucks with a great workhorse engine. Each gen will have it's own quirks in the drive train and chassis. It all comes down to what you prefer and how much you want to pay.

Everyone here knows the'03s and early 04's are the cat's behind. All the benefits of the third gen re-design in a super reliable package with no requirement for a CAT or EGR. Plenty of upgrades out there for anything you want to upgrade.
Of course, any of them should do what you want, these are tough trucks with a great workhorse engine. Each gen will have it's own quirks in the drive train and chassis. It all comes down to what you prefer and how much you want to pay.
I'd say the new 3rd gen trucks are probably going to be more reliable (as in body/interior/suspension) and more comfortable. IF you can find a clean 96-98' 12v that wasn't abused then that takes home the trophy.
Well, I realize this is another "personal preference/opinion" issue, but I have owned ALL THREE generation of Dodge CTD Pickups (1st Gen, 2nd Gen and
3rd Gen) and like alot of the other Members here, my choice would be and still is, the 96'-98' Dodge CTD 5.9 Cummins 12 valve trucks. Why? For the same reasons my good friend above (McMopar) already listed, SIMPLICITY and able to make PLENTY OF POWER! I would add "reliability" to that too.
IMHO, after having owned a now sold 2002 (which ATE three (3) VP-44's in 94,000 miles) and then buying a 2006 Dodge CTD CR (which already has had BAD "Death Wobble" @ 39,000 miles coupled with constant codes and electronic issues) I am convinced that I was destined to be driving the simpler, 96'-98 Dodge CTD 12 valve trucks. Personally, I don't care for all the "electronic control" on the 98.5'-2009 Dodge CTD Pickups.
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John_P
Naturally I'm biased but I would have to say the 96-98 12 valves, plenty of power but still simple to work on, and if you do the 96-97 models you get the older dash layout that doesn't seem to crack and break apart like the 98 up versions.
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