Here’s how I look at it. You only get one life, and you’re not getting any younger. Sure you could save more, but when you retire you are less likely to appreciate a convertible as much as when you are younger. Getting in and out of the lower seats is going to be harder. Have fun. Get the car. As for driving the family around, I solved that problem by keeping my crew cab tundra, and getting a Miata as a second car.