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Towing a boat is hard work, and a diesel truck is often a better choice for towing with it's massive low rpm torque, and improved performance and fuel mileage over similar gas engines while under load. Diesels also typically last much longer than gas engines.
Diesel trucks are capable of huge power upgrades over the stock horsepower and torque. With that power increase, you'll need to give attention to maintenance, and repairs, as well as beefing up that weak stock transmission. High performance Diesel transmissions for going fast, and heavy duty transmissions for towing and getting that power to the wheels is important.
Dodge, Ford, and GM all offer high performance diesel rigs for towing, but with that increased performance comes a hefty price at the dealer, and increased maintenance costs that the dealer often inflates. Local SFBAY Diesel Service shops such as Left Coast Diesel in the San Francisco Bay very often give you better Diesel options, service, and performance at much lower prices than the dealer. LeftCoast Diesel Repair Services SFBAY the best in the area.
If you prefer a do it yourself or DYI sort of performance enhancement, a Diesel Forum staffed by professional diesel mechanics, diesel enthusiasts and diesel gurus can be of enormous help.
One of the things I don't like about my 97 Dodge Ram 4x4 Diesel is the wonky frontend. These trucks came from Dodge with crummy steering and crummy balljoints, tie rods, trackbars, and steering box. It's no unusual to replace all these parts several times over the life of these trucks. Some folks think that Dodge took a normal 3/4 truck with a gas engine, and replaced that gas engine with the much heavier diesel Cummins and did not upgrade all the front end parts. 3rd generation Dodges are better, but still suffer, and 4th generation Dodges seem to have mostly gotten better heavier duty front ends with improved geometry. If you live in Northern California, there is a great bay area diesel service in Concord, and Livermore.