Do yourself a great favor. Get a knowledgeable trailer person to help you select the right trailer and help setup your truck and trailer for towing. As said, BRAKES ARE A MUST. Towing the load is not near as big an issue as stopping it, especially in a sudden situation. And trust me on this, you will get in those situations if you tow.
Like many others here, I have seen or done it all when it comes to trailers. No brakes, no lights, no tag, no safety chains, too light, too heavy, to long, too short, incorrectly loaded, worn tires, and so on. It's just something dumb that we do, especially since "I was just going across town". Fortunately, I have never had an incident worse than a flat tire. Nowadays, my Bother and I maintain a good setup and WE DON'T LOAN IT OUT!!!! Having a gooseneck type trailer pretty much eliminates this.
Today is a much different world. Not only are there are a lot more laws concerning trailers and towing, there is a lot more emphasis on enforcement. Our State D.O.T. folks are writing tickets everywhere for violations and when they stop you, they go over it with a magnifying glass. Here, you have to get a D.O.T. number and be in compliance if you tow a piece equipment such as a SS, even for personal use. Also, there are the looming lawsuits waiting for you if you are involved in an accident and ANYTHING is out of compliance, especially brakes, lights, weight, and GVW. Finally, make sure you are properly insured for towing.