would buying a truck in Delaware make huge dollar sense since it's tax-free shopping?

You say you are a student. I hope you are not thinking of buying a truck with no experience in this industry. Eating a Whopper does not qualify you to have a Burger King franchise, sitting in your garage does not make you a car. Not trying to be hateful, just trying to save you from yourself. Drive a company truck for 2-5 years. Keep track of costs for fuel, , tolls, repairs, your wages, tire etc. After doing this for a few years get a subscription to broker boards and check rates, especially in and out of your home area. Then ask yourself if that is the sort of thing you want to be doing for the next 5+ years while you are making payments.

 

It doesn't mater where you buy the truck, you will still pay taxes and tags in the state you register it in. Taxes for vehicles are charged at the time of registration.

 

Not true.

State of Illinois and many others do not have a sales tax on ICC rated vehicles over 16,000 lbs.

 

WA, OK, MT, IA, AR along with others also charge no sales tax.

 

if you surender your illinois license and come back to illinois you will have to retake the road test again to get your illinois license back---be sure of what you want to do first