Considering a new tow vehicle

You definitely don't need an HD diesel for that truck but it would absolutely do a better job towing that trailer plus allow for more upgrades in the future without changing the tow vehicle. I use my CTD as a daily driver and it's great - very comfortable and gets around just fine. The only dimension that's larger than an equivalent half ton is the height, so it has the same footprint. Personally I think you get a lot more truck for pretty much the same money when you go to an HD model so that's all I'm going to buy going forward. Other than a little bit stiffer ride I don't see how they're any less comfortable than a half ton.