If you are going to tow with a 1/2 ton you better have some good trailer brakes. That skid and trailer are going to push it around. If your terrain is mostly level ground you should be alright. Check your local regulations for trailering and the max trailering capacity on your truck. I have a 98 3500 and would not hesitate to do it but a 1/2 is a lot lighter in driveline. What rear ratio are you running? Mine is 4.10.