I have towed a 40’ Weekend Warrior 5th w/a 2500HD Duramax/Allison - I realized later I was overweight (20 yrs ago), w/o airbags the truck was bottomed out. At 46,000 miles, the Max was leaking fuel into the oil, sold both truck & trailer. I have upgraded trucks twice due to payload calcs. Two questions - is it within the payload limit of the truck? Is the truck big enough to handle the trailer safely? (You’ll know when in wind, hills, etc even if on paper it is able to handle it, a combination of brakes, power, & suspension). IMO the bottom line is legal - if you are involved in an accident & found to have exceeded the payload of the truck, your out of pocket cost could easily exceed what an upgraded truck would cost. At 70yo, I want my risk factor as low as possible - 2021 F350 7.3 gas towing an Imagine 2500. Plenty of braking, power, & payload = safety & peace of mind. I have no desire to risk the equity in our home etc by trying to push the envelope. Beyond payload is safe speed - I used to tow at the the posted speed limit if no trailer speed was posted. Now I tow at the truck limit. We’ve all seen a lifted truck towing a boat or trailer in the fast lane above the speed limit, sometimes with the trailer swaying. If that idiot causes an accident that involves me or my family, I’m going after everything he’s got. Bottom line, it’s like everything else in life - a personal choice.