Should I get a 2020 GM 3500 DRW or a 4500?

Not sure what your wallet will handle, but have you by chance looked into a Frieghtliner Business Class truck (new or used)? Can get w/ air ride susp and seats and possibly cab too. Don't think you'd ever have to worry about weights. Larger brakes, tires, frame and all. Will agree with others tho that service on the road for MD trucks can be difficult and $$$$. I am impressed with the weight capacity increase in the GM line for '20. My problem with any of the big 3 is strapping a whopping huge weight trailer on, grossing 30-35k and either not having the experience towing those kinds of weights AND stopping it. Sure they all say they can tow it, but stopping can be another thing. In the long run, if you still want to stick w/ the GM line and see yourself towing a lot in the future, I'd opt for the 4500 only cuz of bigger brakes and frame. I don't see how the frame of the 4500 is less beefy than the 3500. Air ride can probly be done on the 4500. Tho I said opt for the 4500, service on the road could be an issue, but for pure weight and safety towing heavy, for me the 4500 would win out.

Also, IMO too, GM's 45 & 5500 trucks are really rebadged IH trucks w/ bowtie on the grill. IH made CAT trucks which were nothing more than IH's w/ CAT logos and different trim/colors/dash layout. Marriage lasted just a couple of years.