Hi all!
Location - Central Alberta, Canada
Rig - 2008 Jeep JK Unlimited Rubi on 35's with lots of stuff to make it slower
Trailer - 2012 Canadian Range
I got my start driving things off road with tractors (including a Farmall Model A) back when dirt was still a new invention, and gradually progressed to things as large as a ford 1 ton dually (work truck) before I completely lost my mind and started modifying a Jeep as an off-road/road-trip rig. I guess you can say I have a couple decades of experience getting wheeled vehicles into places that would make engineers cringe.
My current setup is great for "base camp" style adventuring - offroading, hunting, and fishing in one general area. The biggest challenge is the fact that the engine in the JK is fine on the flat stuff with that trailer, but needing to use second gear to get over a mountain pass is definitely not happiness in a tow rig. I'll also say that while it is very "streetable" a JK on 35's is not an ideal long-distance pavement cruiser.
Because I am shopping for a new DD, I'm leaning towards a Chevy Colorado....that can easily tow the trailer, haul a 17 foot sea kayak, and ideally configured so that I can use it as a very quick-to-set-up overnight camping rig for trips where the base camp idea is not really the objective.
I'm still in the beginning stages of thinking through what that will look like, but right now I'm thinking of an extended cab with the 6-ish foot bed, fitted with a hard topper and a roof rack, with the plan being that I'd fit a drawer system in the bottom of the bed, and eventually (probably) a "pop-up" lift system under the topper paired with a canvas camper setup. Yes, sleeping in the bed of your pickup isn't the cool way to do things....but it sure does promote quick setup and tear-down, and works well for Wal-Mart parking lots when on road trips required to reach great destinations.