My family has been farming this piece of dirt for 140 years now and we've had just about every make of truck there is, over the years. The conclusion that I've come to: Unless you're going to have a big fleet of vehicles, it's best to buy a good solid SUV with a towing package. You can buy several good heavy-duty trailers for specialized tasks for far less than the cost of a second vehicle. I keep an enclosed trailer, a dump trailer and a flatbed. The SUV-trailer combination has far more cargo capacity than a pickup bed, and it's much more convenient for a daily driver. Consider a trip to the city for supplies: you load up an SUV then lock it up securely while you go out to the clubs. You can't do that with a pickup. (You may need to beef up the rear springs of the SUV for serious towing.)
edit: I've had similar issues with weekend trips. If your sports involve expensive gear (camp gear, scuba gear, kites, etc.) it's best to be able to lock it up in an SUV. It's too easy to steal stuff out of a pickup.
As for the trucks, just our personal experience, in alphabetical order:
Chevy/GMC: Eh, they're OK. Require a lot of repairs, but they're easy to repair. Good interchangability of parts. Cost per mile is relatively high.
Datsun/Nissan: Very dependable and economical, but just too small. Repairs fairly straight-forward. (Haven't bought one in over 20 years now.)
Dodge: These tend to be the longest lasting ones, but ours tend to be the big flatbeds that nobody wants to drive unless they really need to move ten tons of something. They spend a lot of time sitting behind the barn so we never put a lot of miles on them. Fuel usage is atrocious. The engines have been reliable, but both current ones have transmission issues that have been expensive to fix. Cost per mile very high.
Ford: 100% lemons. Never will spend another dime or day of my life on these. Cost per mile almost infinite.
Jeep: Simple, reliable. Fun to drive. A bit too small and light-weight for any serious work though.
Toyota: Extremely dependable and relatively economical, but ours have been a bit on the small side. Require few repairs, but the repairs are a bit tricky. My 4-runner (300k miles and counting) with a 10-foot trailer will out-haul an F-250, but in the winter time, I have to take off my boots and coat to fit behind the wheel.
Edit: Oops, forgot the cornbinders. International Harvester - so fugly it's cool. When you don't need to go over 45 mph and want to turn heads. Cost per mile? If you have to ask, fuhgedaboudit.