This subject is always a controversial. If you have the money go with the 350/3500. I may someday.
I tow a 5th W with 2200 lbs pin weight with no issues what so ever.
I carried a Palomino M8801 hard side TC (2300+ lbs empty) with no modifications to the truck for a couple of years and didn't know it was on the truck except for gas mileage.
Your rear axle weight (which is what the TC will add) is usually limited by the weight capacity of the tires. Axle weight on my truck was 6200 lbs. as was the tire maximum (3100 x 2 tires). Keep in mind that for the same truck, a gas burner will carry more than a diesel.
How the truck feels to each individual while carrying the TC is a matter of taste, so you may or may not be comfortable with the feel.
My truck handled our current TC fairly good with no mods but was down 6" in the rear. I added air bags to keep the headlights level (the overloads just touching the springs) and tires capable of handling the axle weight. We were comfortable with the feel but last year I did add a rear sway bar which really stops most body roll.
Again, it's all in what you feel comfortable and safe with.