[Altec]

The question is never starting, it is stopping. Are the brakes on it in proper working order, and the same question for the trailer brakes, and controller.

Those things in order, you could make it happen... It is going to be a scary trip though, and you are going to want to go slow, and make sure you have plenty of room for trouble. Towing with a SWB in general isn't good, let alone a half ton. Hauling one of the heaviest of the C/K lines isn't in your favor either...

I am inclined to agree with your Mother that it is a bad idea, but it is possible given good brakes, a properly balanced load, and a slow cautious driver.

Now, is it legal? No...