I used to tow a Prowler 275 CKS 5'er with my old Hemi Half-ton RAM. The dry pin weight was about 1000 lbs and roughly the same tow weight. I added air bags which helped a lot but was in some situations probably, technically over the rated payload of the truck. It handled the weight well but it worked hard at times on the hills etc. Oddly enough, the only thing that really bothered me was high cross winds and when small cars would pass. They seem to create a vortex that interfered the most. I certainly knew there were beside me vs. bigger trucks and vehicles.
So yeah, technically you can do it but I'd still recommend a 3/4 ton for that type of trailer. They're, as you know, just built differently and are able to handle such issues without much fuss, especially with a 5th wheel setup. Basically better suited for towing and heavy payloads whether underrated or overrated for the job at hand.
Even with my current setup which is much bigger and heavier that the previous, cross-winds etc aren't really much of a concern. I can feel them and such but I have no issues getting up to speed, setting cruise and having a relaxed towing experience down the road.