We have done both and it works out financially both ways. We bought both our trucks new. Working on buying another new one now. The newest one is used for towing the horse trailer with the show horses. We bought used cars for the kids when they were learning to drive, mostly Enterprise rentals or they got one of our old vehicles. So as long as one doesn't nickel and dime me to death and is reliable we keep driving it. My 03 needs new brakes for the first time at 215,000 miles, cost will be about a $1,000, new pads, rotors, and emergency brake. That is about 1-2 months worth of payments.