I think I will go test drive one...
Here is the thing... I know to never say never, but I am NOT looking to upgrade the size of my trailer any time soon. We enjoy camping in some spots where a bigger trailer would just be no fun, if even allowed. There are places we camp in north Georgia that don't allow a trailer bigger than 25 feet. Black Rock Mountain is one place... Our trailer suits our needs really well right now and I don't intend on buying a bigger one any time within the "lifespan" of this next truck I buy.
I also do know a bit of what I'm getting into since I do currently tow with a 1500 and have no problems. My ride feels stable, braking isn't an issue, and enough power is there.
I do drive my truck everyday, and that's what is still pushing me to the 1500, but I'd be lying if I said I am not reconsidering the 2500HD.