Won't the newer Explorer last longer than the older used $20k car? I think the decision is not just about how much money is sitting in your garage today, but also about how long you will need the car and how much operating and maintenance will cost over its life. Having an older, cheaper car that you will have to repair more often and replace sooner isn't necessarily a better deal economically. If it were, then why not get a $12k car, or a $5k car? But if you will use it so little (say, 3000 miles/yr) that you will never wear any of your car options out, then I say go ahead, sell, and buy the cheapest car that you can find that will be reliable and do the job you have in mind for it.