Very. Many states have a threshold weight and/or braking distance requirement. But even if there aren't, trust that there will come a time you need to make a hard stop in the rain (or worse, ice and/or snow) and if there is the slightest angle between towing and towed vehicle, you will experience a jackknife of some degree, and in any event, your braking distances will be longer. If you have to brake hard around a curve in poor conditions, you will likely regret it sooner or later. And compounding the danger is downhills. I don't care how many claim you don't have to worry; you do.
My two cents.