I don’t know about this being complicated - it seems to me you’re just overthinking it. I went though the same thing last year as I was looking at a truck. It was pretty simple:
First: look at the exact model of truck including the extra features like a tow package. You should then be able get the towing capacity of the vehicle from the manufacturers website.
Important: This towing capacity is the GROSS towing capacity, it is the entire total load your vehicle can handle. It’s NOT just not just your physical trailer and towing item (boat etc). The gross capacity includes all passengers and gear and fuel etc.
Next - Calculate what your gross weight will be and compare that to the vehicle capacity. If the vehicle rating is above your number, you’re good to go. If it’s less, you need more towing capacity.
This is the only part that’s “complicated”, but you need to sort this out yourself. What is the realistic total weight of everything you will add to the truck at once: passengers, trailer, tow item (boat & motor etc), cargo (food, water, fishing/hunting gear, portable generator), fuel, etc.
Other factors to consider:
As others have noted you should also consider how frequently you’ll be towing and where you will be towing.
If you’re towing loads frequently or in places like the mountains (as you are) then you want more of a gap between the gross capacity and you actual load.
As @GESancMan says - 80% of the gross capacity is fine place to be, but I really don’t think that anyone can possibly give you a definitive answer.
Towing close to capacity or even above capacity is not normally an immediate safety issue (except maybe braking in the mountains), but over time it will wear your brakes and engine and transmission and you’ll have lots of repair costs.
I’ve been at 130% of my capacity on a one time flat trip of 200km (120 miles) with few problems (worn brakes being the main one). I definitely couldn’t do that every weekend, especially on hills or mountains. (A friend’s car broke down on the way back from our fishing trip, so I ended up with 5 big guys, all their gear plus boat, motor trailer etc).
My neighbour bought a boat and frequently towed it with his Nissan Pathfinder, it was maybe 70% of his capacity and after 2 years of towing it 15 weekends through minor hills it blew out his transmission. Towing a trailer or boat once twice a year is different than towing it every weekend.
Only you can answer that.