I've never owned a SRW but I have owned four different 3/4 tons and eight one ton DRW trucks mostly pulling commercially above 25k GCW.
Lots of hype and cheer leading going on by the DRW crowd ..... which is typical
I currently have the '03 2500 Dodge/Cummins 305/555 HO 2wd Jacobs exhaust brake 3.73 NV5600. I also have a 3500 DRW 454 4x4 gazz guzzler beater. I have the DRW strictly for its superior payload from the 4 tires and heavier rear springs for my 16k GN stock trailer moving around locally muddy pastures and stock yards or a muddy work site. I do use the '03 2500 when hauling longer distances as it can muster 12 mpg vs 7 for the 454. The '03 was rated to pull 13350 lbs.
However I use the 2500 all the time pulling my 11200 lb 5er. Zero handling issues in any wind conditions. As you may no the 3rd gen 2500 Dodge 2wd doesn't come with a aux overload spring pack. Huge blunder so I added a set of Supersprings. My previous '01 2500 had the factory aux overloads and had no sag issues carrying the same 5er.
I use the trucks rear axle rating to figure how much load the trucks rear axle can carry which means working with the 6000 RAWR number.
The exhaust brake was mentioned. With a 10k-12k-14k trailer pushing you down the hill you will have a need for a exhaust brake especially if you have the manual tranny. With the exhaust brake I ran 147000 miles on the OEM brakes before adding new pads. Rotors didn't need turning. The truck has close to 220k miles now.
Will you need a DRW or a 3500 SRW or a 2500 truck ?? Depends on how large of a 5th wheel trailer you get and how heavy the pin weight will be.