You will see a LOT of people towing overloaded, and usually, it will fall into one of three reasons why.
1. They don't know any better. They simply haven't taken the time to educate themselves as to what they have and what they are towing. Within that reason number one are many sub categories......"My brother told me it will pull it just fine" A co worker has one just like that and never had an issue. The salesman said that this truck will tow anything I've on the lot..........and on and on and on. Bottom line, the guy that has the truck didn't do his research and learn what was appropriate and large enough to handle the size trailer he has.
2. Lots and lots of folks look at one number......the rated towing capacity of the truck. It says that it will tow 17,000 lb and my trailer is only 16,500. Never mind that the 16,500 lb 5th Wheel Camping trailer is putting 3300 lb of pin weight on a truck that has 2400 lbs of payload. When you confront/discuss/try to talk to them, the first words out of their yap is........"The towing capacity on this bad boy is 17,000 lbs, and I'm under my weight capacity. Bottom line, just like the first example, they didn't do their homework and look at all the capacities of the truck... GVWR, GCVWR, RAWR, FAWR, Payload Capacity, Tire Load Capacity. It's easier for them to justify that they are "OK", because the the towing capacity is not being exceeded.
3. Here's the guy that makes me want to puke! He know how to calculate and figure the numbers, but he isn't prepared to spend the money on a truck that is actually rated high enough to tow what he has. He KNOWS he is overloaded and just doesn't care. And don't get me wrong here, not everyone is made of money, but in my humble (or maybe not so much humble) opinion, if you know that you are buying a new trailer and the truck you have isn't going to be up to the task, then do the responsible thing and either buy a lesser trailer, or maybe a used one and have enough money left over for upgrading the truck too, so that it will match the load it's trying to pull safely. This guy is the one that makes me really mad because he is a me-me-me kind of guy. He doesn't care about anyone but himself and he's going to get the trailer he wants, come hell or high water! Why? Because that is who he is...a selfish, don't care about anyone else's safety, kind of guy.
OK, rant over, resume your regularly scheduled programming! And hopefully, to answer your original question, almost every instance of a truck pulling a 5th wheel CAMPING TYPE TRAILER (not a flat utility type trailer), the truck will run out of Payload capacity before it runs out of towing capacity. And if you are over the rated payload of the truck, you are automatically over the GVWR of the truck. If you are way over the payload capacity, you may be approaching being over the RAWR too (Rear Axle Weight Rating). 5th wheel camping trailer in general, will put ~ 20% of their weight on the truck as pin weight. It can be slightly higher than 20%, but rarely is it lower (Toy Hauler will sometimes do this). And so the accepted way to calculate what truck you may need to safely carry a 5ver Camping trailer is to ALWAYS look at the GVWR of the trailer, take that number times 20% and that will give you a fairly close number to the expected pin weight on the truck. Of course, you still need to add the weight of the 5ver hitch, passenger(s), and anything and everything that the truck will carry, both in the bed and in the cab. When you add up all those numbers, you now know that you need a truck with a minimum payload capacity that is more than that total.