[elhigh]

How often do you tow that boat? If you're shifting it around a lot, I'm inclined to say to look for the smallest vehicle you can find with a Cummins 4BT aboard. The 4BT responds really, really well to aftermarket mods for both power and economy. Whatever truck is wearing that mill is going to be an aero mess, so you'll have lots and lots of opportunity for big, easy improvements early on to get the aero under control.

If you don't tow the boat but twice a year - in at the beginning and out at the end of the season - then skip buying and rent a truck just for the purpose. Then go get a nice used Malibu or something similarly economical and a small trailer for your material handling needs.

+1 on the 4wd ≠ snow mobility. Driver competence has way more effect on getting around in bad conditions than the vehicle; greater vehicle capability usually just means a more heroic vehicle removal effort when the driver gets it sideways and into the weeds.