I've been hanging back on this one wanting to hear what others think before adding my automotive expertise.
I think most of the experiences others have related is both fair and real. Towing a trailer always was, and always will be, a somewhat riskier than normal activity. And there will always be those bad experiences that get burned into our brains.
Once upon a time, trailer towing ratings were indeed a very competitive thing that automakers pushed to the limits. Unfettered by engineering facts, the marketing guys often took liberties unsupported by testing or science. In an unregulated field, there was little the engineering folks could do about it.
I forget the date, but I wanna say someplace shortly after the turn of the century, the SAE (Society of Automotive Engineers) struck a committee composed of engineering reps from each of the automakers to develop a common standard that could be used to put a leash on the sales & marketing folks as well as deal with the plethora of law suits out there. The result was SAE Standard J2807. I remember how everyone got pissed off when Toyoto broke ranks and was the first to certify their vehicles using the new standard ahead of the agreed effective date.
The SAE standard evaluates braking, acceleration, engine & transmission overheating, high speed cornering, sway control, and weight management. And yes, long steep up and down grades (mountain driving) is part of the standard. The standard was upgraded as new issues arose and I'll bet it is still being revised today.
When you see a trailer towing rating on a modern vehicle, you can rest assured that it isn't a number pulled out of some marketing guru's stinky butt.
That said, trailers come in a very wide variety of shapes, sizes, weight distributions, suspensions, and tires. The automakers have no control over the trailer market. The trailer market has SOME basic participation in standards and even the SAE has a few trailer standards. But trailer companies come and go, are often very small, and pretty much do what they want. This leaves consumers to decide what is reasonable. Some consumers do a good job of that and some don't.
If I can offer any advice here, it would be to err on the side of caution. The industry used to use what we called the 80% trailering rule. Never tow a trailer more than 80% of your vehicles GCWR. Some said 75% was better.
I don't see any reason any more to derate your towing capacity for the normal trailer towed by a modern vehicle. But if you have one of those huge long tail wagging travel trailers, or a tall enclosed trailer with internal wall racking, or a Uhaul Moving trailer (usually loaded to the gills), (edit - or a small flatbed with a giant tall heavy First Mill on it -
) install a hi quality sway control system, avoid loading it beyond the 80% rule, keep the speed down, give those highway semi trucks a wide berth, and use some good old fashioned common sense.
But all in all, I personally believe that it's a better trailering world out there than it once was.