Hey Jeff, Sean here. Good to hear from ya. So, I'll chime in here with my 2 cents about towing a Montgomery 23. In the last 4 years we've towed Dauntless in the neighborhood of 10,000 miles. That included bringing her from Florida to Arizona (2500 miles), two trips to Anacortes, WA from Lake Havasu (3000 miles roundtrip each time) and probably somewhere between 13-15 trips to the Southern California coast (which is usually around a 500 to 700 mile roundtrip). Dauntless is probably a little heavier ballasted than Clarity...somewhere around 300-400lbs due to the ballast replacement project I had to do...but I would expect that they are close in all other regards. I took her to a local scale when she was all loaded up to go cruising. Everything pretty much loaded on board except that the water tank was dry. Believe it or not, with all the gear on board, boat and trailer weighed in right at 6700lbs. Like I said, I am ballasted heavier, but that would only account for lets say 400lbs, and I may carry a few hundred lbs more gear than you do, as a minimalist I am not, but still, I would bet that you are tipping the scales at least close to 6000lbs. When we purchased her I brought her from Florida to Lake Havasu with our Chevy Tahoe, which was not a comfortable ride. The Tahoe had plenty of power but the trailer was in charge and I was in fear of having to make a panic stop the entire way. Even with stainless disc brakes on a brand new trailer, stopping was a worry. Also, I think due to the short wheelbase of the truck, the Tahoe had to be constantly "driven", as it just wanted to hunt all over the place constantly. I was fortunate and found a great deal on a truck that is at the other end of the extreme and was able to acquire it. I would not say that a 1 ton diesel dually four door is necessary, but I would say "what a difference" when it comes to the fatigue factor of driving. This truck does not even react to the trailer and always feels fully in command, even in that dreaded "unexpected stopping scenario". You specified a 1/2 ton truck. My two cents is, yes, you could tow the boat with a half ton, but it's surely not the optimum and certainly not going to give you the best safety factor. The bigger suspension and brakes that you will get on a 3/4 ton will be of great value. The truck won't work so hard carrying the weight, it most likely would have a larger engine so will last longer due the fact that it's not going to work as hard, and most importantly, the truck will command the trailer and not the other way around. Another difference is most 3/4 ton trucks have larger tires sizes with heavier side walls that also will help with load stability and limit side to side movement. One BIG suggestion I would have is to shy away from a short-bed truck for towing. The longer the truck is, yes, the wider the turning radius, but the better it will track and resist hunting around due to influence of the trailer, especially in a crosswind. Another place the bigger engine will pay off is in downgrades. With our diesel, I can kick it out of overdrive (yes we can tow ,believe it or not, in OD as long as we are not climbing), and descend a 6% grade without using brake pedal to control the speed just by downshifting appropriately. A smaller engine is probably not going to give you that much back pressure and unless you are using electric brakes, which most of us are not, your only option is to keep applying the truck's breaks as you descend. We all know that you can only do so much of that before things start heating up. My suggestion, especially if one is financing a truck anyway, is if you are gonna tow something like this seriously (other than back and forth to the local ramp) spend a little extra each month, buy more truck. In the long run it'll last you longer, but most importantly, it will pay off hugely in safety and comfort. 4wd certainly is nice to have, but in 4 years we haven't had an issue except at one slippery local ramp. Other than that we've launched all over with no problems. We are a dually, though, so that may give us some extra traction. Like I said...just my 2 cents which is worth nothing more than anyone else's here and is mostly just opinion. :-) s PS...If you decide to tote a 85lb polar bear around with you, as we have...the four door cab is a must! ;-)