I've grown increasingly aware of the underlying fact that this is such a subjective question that it is extremely difficult to answer in this forum. People will throw out all sorts of limitations that have no objective grounding, while others will create all sorts of justifications to throw caution to the wind. The simple reality is that actual weights, as rated for the specific truck and trailer, are the only truly objective measures one has. The problem, of course, is that being within those ratings, as you are stating, does not necessarily mean the driver will be comfortable with it.
For us, I have a 2019 F150 max tow and pull a 35' trailer that is 8,000-8,400 pounds, loaded, depending on water and gear. When the full family is along for the ride, I am right up against my GVWR (but not over), and about 1,500 pounds below my GCVWR. This is a new combination for us, but I did about 5,000 miles this summer with no concerns. When the winds were gusting at 25+
a few days ago I could feel it, but it was never uncomfortable. Others, of course, would not feel the same!
Since we only do 4-5 trips per year with most being within 500 miles, this works fine for us. If we were full-timing or hauling multiple 1,000+ mile trips each year, we might see it differently.
