Steve Hoelscher, owned a transmission shop for years, has posted a lot of comparative info on various towing thread on SCCAForums.
Here is an example:
http://sccaforums.com/forums/1/386668/ShowThread.aspx
Overall, he like Fords for relative reliability, especially of automatic transmissions.
Nice Pros/Cons from one of the posts:
Chevy, Dodge or Ford: As you will find from reading the responses and looking around the various forums, each has its strengths and weaknesses. Dodges typically get the best mileage. Chevy (duramax) has the most power and Ford the best quality/reliability. Having driven several examples of all three, I like the Fords for driveability, handling, ride and comfort.
Auto vs Manual: Lots of people will tell you the manuals are more reliable and cheaper to live with. This isn't exactly true. Dodges has as much trouble with their manuals as automatics. And typically, the manuals were more expensive to rebuild. Add to that the cost of a clutch every 100+K miles and note that clutches for these trucks aren't cheap. Ford's ZF is a good unit as is the GM NV but they don't last forever. The later Dodge autos aren't bad and there are any number of upgrades out there. The Ford 4 speed and Torqueshift are good units as is the Allison in the Chevy. And an important note about the Allison. People are finding out that the Allison isn't as strong as they may have been lead to believe. I have seen a number of chipped trucks kill their Allisons towing modest loads with a heavy foot.
An important point about the auto/manual decision. 20 years ago I wouldn't have considered towing with an auto, now I really wouldn't want to tow without one. Modern automatics are excellent and give nothing away to manuals. Modern autos, 4 - 5 or 6 speeds, with modern locking torque converters get just as good, or better, mileage than manuals and are much easier to live with.
2 or 4 wheel drive: Unless you need 4wd for snow or off road, its unnacessary for towing. 4wd adds cost, weight and complexity to the driveline. A transfer case overhaul is nearly as expensive as a transmission overhaul. Plus, you have the additional driveshaft, CV joints and front drive axle and diff to maintain. And if gas mileage is your goal, 4wd is heavier and adds innertia to the driveline, all of which lowers mileage.
At what mileage do you start looking at repairs: Of course that depends on how the truck was maintained. Most any modern truck, with reasonable maintenance, will run 100 to 150K miles with little beyond normal maintenance. At that point, things like alternators, starters, radiators, hoses, injector pumps, clutches, transmissions, etc... begin to start going. But a well maintained truck may go to 200K without much issue. The engines on all of them are likely to go 300+K miles without too many issues. The gas motor in my van just passed 290,000 miles, most of which are towing, and its still strong and reliable.
Advantages gas/diesel: Diesels typically get better mileage, especially towing. But diesels are more expensive to operate (fuel filters, water separators, oil changes, coolant changes, etc... are all more frequent and more expensive. And with the price of diesel running higher than gasoline, the cost of operation (dollar per mile) might actually be closer than you think. Add to that the higher purchase cost of the diesel truck and you will need to run it considerably longer to realize the savings. So power is likely the major difference and there the diesel has the edge.
Ford F250/350s with 6.8 liter V10s are cheap by comparison to their diesel brothers and tow nearly as well. Mileage will be less but not huge. So if you amortize the cost to buy, maintain and opperate the V10 gas truck to any of the diesels you may find that over the life of the truck the costs may not be that different. Its worth considering.
Dick