I'm a professional driver in the RV area. In most states you would be required to have a CDL with a combination endorsment. If you were to do this for money. So my advise would be to do the same in your private life so you would be aware of all the in's and out's of towing such a rig. The only other thing you have to watch out for would be the overal length of this set up. Check with the State of Kentucky for their laws covering this.
And good luck, you might just need it.