Wow. This post started while we were camping and is on page 6 already.
We started with a bumper pull travel trailer.
2 years ago, we upgraded to a 5th Wheel.
Our trailer is ~37' long.
I worked the weight of the trailer my wife wanted and went truck shopping.
I rejected 3-4 trucks that I really liked because the payload was not enough.
I bought a RAM 2500 shortbed with the Hemi (gas).
My truck pulls the fiver fine and is within all weight specs. One note about diesel engines - the diesel will weigh approximately 900# more than a gas engine. So, your RAM 2500 diesel with the same chassis as my RAM 2500 gas will haul less trailer than mine. I was shocked at this difference in weight.
Backing the trailer is just a matter of getting used to it.
I could back my 34' TT like a Commercial trucker when I got rid of it.
The 5er is much different and I am just getting to a point where I can back it in to my driveway on the first try (most of the time).
I always start looking for fuel as I approach 1/4 tank of gas left. Don't pull in to a small station with little room. When traveling, if you pay attention to where you are, you can typically find stations with room to pull in and pull out without a lot of trouble. I have backed out once or twice. It's just what you do.
Our set up is a breeze compared to our TT. I back in. We put blocks down and extend the supports. Then my wife pushes a button and raises the front until I am clear to disconnect. Once I move the truck, she pushes another button. Approximately 60 seconds, the fiver is leveled and stabilized - automatically.