Ah, this is the feedback I am looking for. Thanks!
I have a Wildwood X-lite that is 6k empty and 7.5k gross. My 1500 actually pulls just fine with the 5.7 and 3.21, but there are two things I want to upgrade. First, the payload of the 1500 is too small and limits what we can throw in the bed when towing. Second, the trailer is 33.5' long and I would like some more stability when cruising on the highway.
Your thought proccess and wanted improvements are exactly why I moved up to my 2500 from a 1500 Chevy. One of the best decisions I've ever made. I have no plans or desire to go back to a half ton truck, unless I get to the point that I can't maintain it.
You'll get both of your wanted improvements with a 2500 HD and towing performance will be good at that weight with the 6 speed. I'm confident I could go another 2k lbs in loaded trailer weight with my truck with no problem at all.
As I mentioned above, the advice to get the 8 speed if you can is sound, but if you cannot, I think the 6 speed would be fine for what you'd be asking of it.
My truck has tons of power, even in the mountains. If I was up over 10k loaded trailer weight, I'd consider going to a 3500/Cummins, but don't need that now.
Good luck with your decision. If you go for the 2018, ensure the steering drag link has been replaced by FCA (not just welded under recall)