Lots and lots of variables,
What kind of budget are you looking at for a vehicle?
Do you own your own house?
You can get into wakeboarding/surfing including a tow vehicle for under twenty grand or you can blow that much on a boat's stereo. You wouldn't be out on the water with the latest fad, but you don't need to either to enjoy a weekend on the lake. When one of my companies went belly up, I sold my '03 Natique that I bought brand new and spent two years wakeboarding behind a old Ski Sanger that I bought for $5,000 and sold earlier this year (after it sat on the side yard for two more years) for $5,500. If you don't think you can fix up an older boat to be sweet, check on some of the boats here on this forum, (Berg's for one)
So, if you are looking at a pre-'06 LSV style boat, they are relatively light. My personal tow vehicle is on '01 F250 with the 7.3L Powerstroke (on it's third tranny!) The newer 6.0Ls had their problems, but can be fixed/prevented. Look around and grab an older F250 or F350 four door if it is not going to be used that much. By the way, I own my own company and I would love to drive someone else's Prius (I am cheap).
Last week I had decided to buy a new Suburban to tow my RZ4 which is a pig (wayyyyy heavier than my Moomba) so I could carry all the teenagers also. After looking at what Chevy offers for $60k+ which is a small V8 on a half ton chassis, I have decided to pass for now and start looking for a clean low mileage diesel Excursion or test drive the new 6.2L gas Denalis (opposite end of the spectrum!) But right now for my money, buy used then with the money you save, purchase real estate.
BTW, if you don't own your own home and you spend $40k+ on a truck, you are a fool -- unless you got rich parents then go to town spending their money!!!
Just seems so wasteful spending that kind of cash on truck to tow a small boat.. $5k max for me...
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Once my lease is up on my car I'm going to strongly consider going to an Ecoboost and only having one vehicle. I like driving a truck every day, but they are just getting to the point of decent enough gas mileage to do so. I need the full 6' bed for my fifth wheel and if it's my daily driver I need a quad cab, and it looks like Ford is now making the F150 with the full bed with a quad cab since I've seen a few on the road. My big hang up for trucks as a daily is I need quad cab with the full bed, and that's been only a 3/4 ton until now but I don't want to only get 12mpg (not willing to pay for a diesel, too expensive). Plus the Ecoboost is a beast, higher tow rating than my 3/4 ton dodge. I don't think any of the other manufacturers are doing quad cabs with full beds (except Dodge, but their "quad cab" is basically an extended cab with full rear doors, the Hemi is a hog, and their new V6 with the 8speed trans that gets 25mpg can't tow much).[/QUOTE]
The new 2014 Chevy and GMC have a 6 foot or longer bed in the 1/2 ton
I really like the new design (I've always liked Chevy/GMC trucks best for exterior design), and I was raised on GM since I grew up near Flint. My parents have never bought anything but a GM product, and a significant portion of my family and my wife's family work for or retired from GM. I've always just bought vehicles based on my needs, but I've always had a soft spot for GM since I grew up with their vehicles.
After 2 Chevy Avalanches, I really like the GM product. Since I have had my F150 EB, I don't miss the avy at all. The ride quality is just as good (if not better), the rear seat room is much more, and the EB is something else. As far as gas mileage, I'm pretty sure the Ford EB or 5.0 and the GM 5.3 will all be pretty close in gas mileage. I know enough people with Ram and Tundras to guess they will be slightly (or more) worse on gas.
I really like the gauge package in the Ford with the infomation screen. It tells a lot of info. Ram and GM have similar info, just not as easily viewed.
As far as towing, the EB is pretty stout. Looks and comfort will be subjective to the consumer. The towing ability of the EB is impressive.
As with anything, test drive for yourself.
If he has the means to go out and get a brand new truck, it sure seems like the EcoBoost is a top contender from many people!
There are a lot of good vehicles recommended here. I'll share a quote that I heard when I was looking. "Almost any SUV or truck will tow a boat. The issue is stopping it". Whatever you decide to get, ensure that it is big enough to stop if someone pulls out in front of you while towing.
The reason to be concerned about stability is not just vehicle size and suspension. There is a less-known failure mode that can lead to a "wild ride" in response to input from the road or an abrupt course change: frame flex. Body-on-frame designs can transmit flexion like a wave, making the truck bounce and buck instead of letting the suspension damp everything to get tires planted back flat on the ground. This is one reason why, among many older models, a 3/4-ton or 1-ton "feels" so much better with heavier loads. Some recent half-ton models, such at the F-150, have significantly improved this in the last few years. Certain well-built SUV's, such as the 4Runner, can tow better than what you'd guess for their size because their bodies limit flex.
Frankly, most full-size and mid-size vehicles will be fine for your boat unless they have some particular weakness. For example, I avoided earlier Pathfinders (which were big enough for my previous boat) because independent reviews said that they had weak brakes that were only adequate for the vehicle by itself due to anti-lock brakes. If you plan to upgrade the boat later, assume that when truck shopping.
The best way to know for sure is to tow a boat similar to yours during the test drive, and to have a somewhat challenging course planned. Since you don't yet have a boat or an adequate tow vehicle yet, soliciting help from a friend with both items would be in order. New vehicle sellers will probably not allow towing (because the engine and brakes aren't broken in), but it should be fine for a used vehicle.
And after writing all that, I still say that renting a tow vehicle is the best choice for the OP for the next couple of years. Virtually any vehicle costs thousands per year to keep. Spend $1000/year on a rental to reduce costs while getting "doubt removal" with recent models.