^That's a good point I forgot to make. My 'truck' does kinda bog out on huge hills. Not super bad, but you can definitely feel it. If it downshifts though, it gets up the hill just fine. It's only when there's a ton of pressure on the transmission that it kinda 'blahs' on me.

I've never had a problem stopping my trailer in wind/ice/rain/etc. I have a nice set of brakes, and a good brake box (with the emergency stop jobby in it.)