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I've been operating diesels for several decades as well, but haven't transitioned into any of the truly modern versions with all the emmission controls etc. So I don't doubt that the newest ones are more complicated and costly to maintain. But with these less complex engines I've operated, my maintenance experience has been characterized by low-cost and simplicity. Regarding oil change intevals, I thought I'd mention that my current diesel daily driver has a 10K miles oil change interval (synthetic required). That is significantly better than our other gasoline-engine-powered vehicles.

There are pros and cons to choosing diesel over gasoline and vice versa. But any large displacement engine with high-cylinder count and multiple cylinder banks is going to cost more to operate and maintain over the long haul, as compared to smaller engines with fewer cylinders in a single bank. So I think to a certain extent, higher operating costs go with the territory when looking at heavy haulers such as these pick-up trucks.

If I was in the hunt on the used market, I would stress overall condition more so than diesel v. gas. There are just tons of good gas-powered trucks out there to choose from, but not so many diesels. I think the OP could easily find a solid gas-powered pick-up within his budget, that would haul his boat just fine. But finding Garris' truck might be tough.

As an aside -- for those with less demanding towing requirements than the OP -- Chevy is releasing a new Duramax diesel-powered Colorado (their smallest pickup). It has a 2.8L 4-cylinder with roughly 180 hp and 369 ft/lb of torque. The 4WD version is rated to tow 7600 lbs and, while it hasn't received an official EPA mileage rating yet, there is a good chance it will exceed 30 mpg on the highway (unladen). The 4-cylinders in a sinlge cylinder bank should help to keep maintenance costs down, as well as the 7500 mile oil change interval. It might be an attractive option for anyone with the 18-22 foot Whalers, that also needs a reasonably economical daily driver.