Questions for the weight police

I had a 26' (30' hitch to bumper) trailer with a 2002 Tahoe and I know I have a 30' (35' hitch to bumper) trailer with a 2010 Tahoe. For 100 mile trips or 1000 mile trips, you'll be fine. I've towed all over the country, lots of local trips and many trips from FL to MD and vice versa. The only time I've struggled is climbing mountains in the Denver area, but it still got the job done. I haven't towed with anything else, so I have nothing to compare it too, but I know it's not an 'ideal' towing situation. With that said, I drive comfortably and have very little issues with sway or braking. I think you'll be fine, especially if your long term goal is to go to a 3500. I've been looking to upgrade to a 2500, but right now it's more of a want than a need. I'm certainly maxed out on specified weight limits, but make sure to not go over and I confirm that on the scales whenever I add more stuff than normal.