My recommendation is to look at the worse case scenario. What's the realistic pin weight of the trailer after you've got stuff loaded, NOT the published pin weight which is usually lower than real life.
How much instability will there be on windy days? When a big semi truck or bus blows by you, are you worried about being pushed half a lane over by the compression wave?
If that car in front of you short brakes all of a sudden, does your tow vehicle and trailer brakes have enough stopping power?
How's the turning radius when you have to maneuver into a tight spot?
Some vehicles are just better at towing.