I tow a 18ft trailer with a Kubota L4400 with my 1992 S10blazer and it has the power to pull it no issues, I dont have any hills so not to worried on that, but brakes yes indeed you will need them on the trailer, And as the other person posted your going to have to fiddle with the wieght of where your car sits on the trailer, your going to want at least 700lbs on the ball hitch, basicly if 2 guys can lift up on the tounge that will get you in the ball park, its best to a bit more than not enough, if your trailer is wiggling down the road then you dont have enough weight up front, and all it might take is moving the car 2 or 3 inches can make all the difference in this. Even with all this done I would try to drive faster than 60mph