I got a new truck last year because incentives were good and they offered me more than what I paid for my trade. I paid less for a new one than I would for a used one. Crazy.
That being said, growing up I hauled a 6×12 v nose enclosed trailer, single axle with 2 bikes a toolbox and a bunch of parts using a 1998 chevy blazer with a v6. Braking was where it seemed to struggle the most if I remember correctly. It pulled the trailer surprisingly well.
My issue with a small truck is they're so close in price to a full size and the fuel economy isn't that much different if you're looking at a 4x4 which after this winter, I'd recommend unless you're getting a 4cyl. Anything more and I have found you're more likely to spin. 4cyl seemed to track a little better than a v6 in 2wd. The parts really aren't too much different as far as normal wear and tear items. I wanted a Colorado or Tacoma but price wise it made more sense to buy new full size.