OP, it really depends on where you live. In CA I would never buy a 2WD truck because regardless of the top of the line snows and your driving ability, the CHP requires anyone without 4WD to use chains. Also, every trailhead I've ever seen is simply a parking lot with a trail head right there. The truck should technically never have to leave the road because if you have to go up a snowy dirt road, the sled can go up that anyway. That's just how I've always seen it done. Anyway, if your cousin puts the sled in the bed, it wouldn't be too bad. You should be more worried about the fact that he has a 4 banger. A 4 banger will get fucked anywhere above 5000 feet. I drive a 4 banger right now and there is a significant difference in power at 7500ft. vs 4000ft. I can't even imagine how bad a 4 banger truck with a sled and gear loaded at that elevation would suck. You and your cousin are both jackasses, except he's ignorant and you're a whiny bitch.