It all depends on how much of a load you are towing, over what distance and type of terrain. Don't forget about having a little extra to pull the boat out of the water in a steep ramp. Unfortunately these days family sedans are unable to do double duty so unless you can find a 70s car you must buy a truck. Unless in your line of work you can use a truck then the sensible thing would be to purchase used and the cheapest that could do the work. Obviously if you are towing a big assed boat for long distances in the rocky mountains you will need a more expensive truck than if you are towing a 3000# boat 1/2 mile in flat terrain. With distance comes the issue of reliability; if you are towing 1200 miles away from home you need a newer and more expensive vehicle than if you are just going around the block. Make a list of your requirements as far as capacity, mileage, model year and define the most that you would be willing to pay. When purchasing used warranties are limited and you can either get a gem or clunker. Unless you have confidence in your abilities have a trusted mechanic check the vehicle out. Japanese trucks have a better reputation for reliability than the Americans but that is in general terms. All these trucks are assembled in the US so don't feel unpatriotic by choosing one over the others. Look for the best deal that will offer reliability and capability to do the work and remember that your needs are likely different than those of the next guy who may have a different criteria for his ideal towing vehicle.