Tacoma towing trailer in snow/ice/wind

Hi, I have a 2014 Tacoma 4x4 Double cab. I'm looking at getting a 10'x6' enclosed trailer to convert to a little ski bum camper. I need to know how well it might tow in winter conditions snow/ice/heavy wind. I want to eventually drive the west coast from LA to Alaska in march/April 2018 and am worried about the towing capabilities in snow, even with 4wd on my truck. Any advice/suggestions/comments would be appreciated. Thanks

 

Do you have a guess roughly how much the trailer will weigh after you modify it? Anything around 3000 lbs or less shouldn't wag the truck too bad. Just be aware of increased stopping distances if it doesn't have trailer brakes... I slid through an intersection in slushy snow with only about 1700 lbs on behind. It's unbelievable what a difference it makes.
What you're more likely to discover is how hard the truck needs to work in a strong headwind because the front of the trailer is catching so much wind. I towed a U-Haul 10x6 from Edmonton to Winnipeg (1600 miles round trip) and coming back with a roughly 40 MPH headwind I didn't feel comfortable pushing the truck so hard it would maintain highway speed (only had about 2000 miles on it at that point)...
Since installing the topper, no more trailer induced wind resistance.
Do you have a canopy?

 

I should add, the supercharger has helped immensely with towing

 

very cool idea to make use of the trailer into a mobile camper and take it to Alaska, nice adventure.

 

Do you think something like this (roof mounted wind deflector) would significantly reduce trailer induced wind resistance? I have a tonnau cover but no topper. Or will the open space between the cab and trailer still cause too much turbulence?

http://www.campingworld.com/shopping/item/48-x-22-wind-deflector-polar-white/68800

 

I've never tried one of those, but I think it would move the air up enough that the turbulence between the back of the cab & front of the trailer would be reduced quite a bit.
I was on the verge of buying one when I lucked into my shell

 

I just towed a 5x8 u-haul from Phoenix to Eugene with my V6 2010 Prerunner. Truck was loaded to the top of the camper shell and the trailer was fully loaded too. I was probably over the weight limit a little, but I had modified the rear springs awhile back. No tail wagging the dog, but watch the speed because it costs a bunch in mileage. Keeping at 55-60 I got about 14-14.5 mpg, but I hit some strong headwinds from Las Vegas to Tonopah 35-50 mph and my mileage fell to under 10. I did a similar trip years back and 65-70 was 11-12 mpg and 55-60 mph was 14-15 mpg. If your going to be doing this a bunch a full size truck may be a better option. I've towed with my brothers Landcruiser 5.7 and the trailer only cost 2mpg.