I have a 6000# 28' Travel trailer (lurking here just because I'm planning on a fifth wheel at some time). I've towed with the following,
1500 Crew cab, works but grip the wheel very tight and always aware the trailer is back there.
2500 Ext Cab 2500HD short bed Duramax, Much better! no problem with hills and my hands are not tired after a two hour trip from gripping the wheel. But, I still know it's there and big trucks or strong gusts and you do feel it!
3500 MegaCab Cummins, dually. Only problem, you have to remember it's there.
I would get the DRW, I think you will travel more relaxed.