I fixed the problem by buying a Silverado 2500HD.
The truck I had was a lease with a really low buyout. I had every intention of buying it until I ended up with a bigger camper. I was asking the questions because I was still debating on buying it and using it for a few years and then upgrade later.
In the end, it didn't seem logical to buy it with it so close to it's limits for the trailer we have.
The next trip is in a few weeks. Around 250 miles each way into the Catskills, so there should be few good size hill climbs along the way. I'm anxious to try it and am anticipating a more stable experience, so to speak. I had a 2500HD a few years ago and I know they have a different (better) feel to them while towing. The 1/2 ton never felt as good to me right off the bat and that was with the smaller trailer (28.5 feet, roughly 7500 wet plus 500 or so for passengers).
Thanks for all the feedback.