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I have a hitch for my current truck and honestly a dump trailer wouldn't be a bad idea anyway for some use cases, but even if I had one I'd probably only use it when I had to. The convenience factor just being able to hop in and drive, or having the truck bed with you when you didn't plan on moving something just wins out.
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I think there are still tradeoffs of conveniences. A separate vehicle is handy for being able to slowly collect things to get rid of in one later trip, or to store something you just got until you're ready to put it somewhere else (I've got what remains of a 1/2 yard of sand sitting in mine). And being able to just dump something and drive away is quite nice (especially when you can put it into the trailer using equipment to begin with).

On the other hand, I've never experienced being able to just haul something without a little planning first, so I don't miss it.

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Trailers aren't a silver bullet. I own multiple trailers (one even has a crane on it) and will still use anything else given the chance because it's just such a hassle once the empty weight of your trailer gets above what's convenient to move around by hand (which it will if you want to beat what a half ton truck can do, not what's within the rating, but what it can do).
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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 full length bed that can support that whole pile.

And sure I'd think 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?

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Not wrong. I combined my truck and SUV budget and bought a used X7 m50i and a small utility trailer. No joke it's the best pulling vehicle I have ever owned. Super heavy, super grippy, in trailer mode the torque comes on fast. It's brilliant. My old 03 Silverado sits even more now.
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