If you are willing to go with a CUV/SUV, I have to say that Mom's Acadia (Chevy Traverse) is actually changing my mind about GM. She has had a string of CUV/SUVs from GM that were questionable: 91 S-blazer, 94 S-blazer, 06 Trailblazer, 09 Caddy SRX. When she got this 2018 Acadia I thought, oh boy, here we go again. I was wrong.
Tow capacity of 5500, more power than you need, luxury that puts an X5 to shame, and really impressive interior fit and finish. Color me impressed. I towed my boat with it a few weeks ago (3500 lbs) and I loved it.
Taco is the sweet one. In your price range, you can pretty much count on twice the miles compared to a Colorado or other compact pickup which chaps my butt a little. Yeah, they're a better truck, but not THAT much better. If I were buying new, definitely Taco to keep more money in my wallet when I sell it, but it's hard being on the other end and buying that used Toyota.
Colorado doesn't win any beauty or performance contests, but it is a good, solid, boring truck.
Not that they're likely in your price range yet, but read all you can about the new Ranger before putting down your money. Every truck magazine I picked up last year did a comparison test with Colorado, Taco, Gladiator, Ranger, Dakota, Frontier, etc. In every one, the Ranger took last place. They hated them. In a surprising twist, a decade-old Colorado design actually beat the Taco in some of the magazines to take top spot.
If you're willing to do SUV/CUV, I would look to FJ, Acadia/Traverse, or 4-runner. In trucks, I think it's pretty much a rusty-framed Taco or Colorado if you believe the magazine guys.
Just be careful what generation of any of them you pick. Anyone else notice that the latest gen Colorado looks bigger than a GMT800? And a new 1/2 ton truck looks as big as a 1-ton GMT800? Geez trucks are getting big. I just don't want the other driver to slap you silly when you bring home a "compact" pickup that is bigger than a full size from 10 years ago.