The two strongest contenders to fit the OP's needs are not on the list:
- Ford F150
- Honda Ridgeline
Among the trucks listed in this thread, the Ridgeline is by far the most versatile and the best daily driver (independent rear suspension). A short test drive on a bumpy road will bear this out (as it has for many Ridgeline owners who came from other brands). I get 24 MPG US on the highway. Among the mid-sized trucks, it is the only one that has a full-sized cab that can comfortably carry five adults, and the only one that has four feet between the wheel wells for carrying standard construction supplies. It is the only truck with a trunk, which is shockingly handy. It will probably remain reliable for twice as long as the GMC or Nissan. It has the best slippery-road handling among pick-ups. It only handles moderate off-roading, and can only be lifted 2in. Some aftermarket accessories will cost more due to its unique shape.
BTW, disregard MSRP, as Honda oddly does not advertise rebates. Also, the people who wrote some of the Ridgeline commercials appear to be on some serious drugs. Eesh.
The Ridgeline will tow your boat very well. Your older LSV will be well within its 5000 lb towing capacity. I did same-day head-to-head comparison with a 1997 Silverado (w/tow package) for handling while towing my XLV. The only thing that the Ridgeline could use is extension mirrors. It is designed and now assembled in the U.S.A. See
http://www.ridgelineownersclub.com/forums for a deluge of information, including honest comparisons by many people who were really doing their homework while shopping.
I probably would not pass up a Touareg if some fantastic bargain on one crossed my way. :-) However, the OP wants a pickup truck.
The Avalanche is also very versatile and has rear coils springs for better comfort... but again I would not buy one because is made by GM.
Ford seems to be the only Detroit brand that seems to finally "get it" with respect to quality, and that's only recently. They also have a new line of efficient engines for their trucks. Both Ford and Honda are expected to have entirely new offerings in their trucks by next spring, so my advice is to wait until then if you can stand to do so. Then you'll have both old and new models from which to choose for these strong brands.
I strongly agree with the other posters about 4WD. You will probably encounter a situation where it will prevent a VERY stressful issue, whether or not the boat is involved, compared to a RWD-only truck. It will probably avoid a great many marginally troublesome situations, too.