The thing about equipment is no matter what you've got, you're always going to want something bigger.

You just need to cover the bulk of uses, not every last thing you might need to do. I think the light SUV + utility trailer is a pretty good sweet spot, even better for many things than a pickup truck on its own. Like have fun lifting 20 sheets of plywood up onto a pickup truck and back down, assuming you've even got one with a long enough bed to support that whole pile.

And sure I'd imagine larger trailers get to be a hassle to move empty by hand, but isn't that what having more equipment is for? And isn't that well into the tier where you need a truck for a tow vehicle regardless?

Unless it's so small it roughly equals the utility capacity of a half ton truck a trailer is a big hassle. People choose to pay more for a truck because it "just works" with "no thinking" for a wide variety of stuff.