Hypothetical what truck - Day dreaming edition (ie the hotlink thread is a better use of time)

Avid boater here. East coast of Florida transplant living on the west coast which means my scuba diving and Bahamas trips access are limited. Originally planned on moving back but the Tampa Bay area is growing on me and the east coast is turning into a cluster.

Anyway, we went spearfishing 30 miles off shore this past weekend and now I have the itch for a bigger boat. A bigger boat means I need a replacement tow vehicle for the Corolla. In this life goal scenario we would live on the water and this hypothetical boat would stay on a lift. What I need is a truck for the 6-10 times a year that the boat would need to be towed to the Keys or to the east coast for a Bahamas trip. Otherwise it would stay in storage. So I want a highway cruiser that fits at least 5, bottom of the depreciation curve and repairable by a knucklehead like me. It also needs to be able to tow 10k pounds. Cold AC a must and cruise control a plus. Otherwise basic is better.

I'm thinking a ~2000 F250 with the 7.3 + a manual transmission. Maybe the previous generation would be better. Any other ideas? Purely hypothetical and once I get back to grips that I can't buy a $100k boat I'll go back to thinking about Volvos.

If you're planning to pull 10k lbs regularly, I'd be looking at an F350, not a 250. Probably don't need a dually though.

The 7.3 / 6spd is a good drivetrain, especially in 02/03 where the manual trans 7.3s got a bit of extra power (275hp vs 250 for the autos and 235 for both in the earlier years). Only thing is, you'll pay a bit of a premium for the manual trans and they can be tough to find.

I just went through a very similar usage analysis and ended up with a '96 F250 with 7.3L turbo diesel. It's an XLT, so it has cruise and air. I went for an auto so I wouldn't have to deal with the manual trans on boat ramps, and extended cab because there's only two of us and a dog. I love that truck. It is the most comfortable thing I've ever driven over a long distance, as long as you have a little weight in it.

To seat 5 you will want a 4 door. They're pretty rare in the old square bodies, and a 4dr, manual, 4wd is the most expensive combo you can buy. They'll cost double what an extended cab 2wd auto goes for. The 4dr combo is much more common in the 99+ super duty style you're thinking about. I'd say you are looking at the best option for what you want, although I personally like the older trucks. I like the looks much better and I find them to be more comfortable.

Even bigger boat and a few extra days of sailing from the West Coast? Depends on where you are but would only add a overnight or two unless you are way up north.

If you re going to use it 6-10 times a year do NOT buy a diesel. (They don't like to sit.) - will restate due to feedback.

If you are only going to use a truck that often, then you are unlikely to be taking advantage of a diesel. You will pay a lot more for the truck you have described than you would for a gasser that would do the job. As others have pointed out - the requirements that you have listed basically would mean that you would be chasing a unicorn.

Get a GM crew cab with the 8.1L and Allison, and you will likely be much better off in the long run.