How does moving in the military work?

Many of us can answer this; however, I recommend that you contact your transportation office. Which post are you located?

First of all there is a limit to the weight of HHG, you need to ensure you get that and transportation also has a way to estimate your weight. As for vehicles unless you have a very large family the Army pats you to ship one, the other is on you. I promise that the few hundred bucks it takes to ship a car (provided you have it) is well worth the stress it takes to travel with two cars. Also look into partial Ditty move which helps you with must have items while waiting for your HHG. You can rent a trailer and to weigh the car and trailer empty then load them up with all your gear and re-weigh. There is more, just get in to see transportation. Thank you for your service.

Check your orders, or have a personnel type explain what you are allowed. When I was in, I towed one car with the other, and the next move had one shipped. They each have their pros and cons (should have some experience towing going through mountains and such). Sometimes, you can get your orders amended if need be.