Buy a Miata! The second-generation “NB” car (1999-2005) is now old enough that it's easy to find decent ones under our price cap. If you're looking for a cool toy, look no further: rear-wheel drive, lively handling, rev-happy engines, delightful manual gearboxes. And did I mention it's a convertible, all the better for soaking up the sun all summer long? Going with an NB over the first-generation NA means you'll get a little bit more power (depending on model), the availability of a six-speed manual (again, depending on model), and a car that's just plain newer and fresher than the aged NAs. Still not convinced? I bought my own Miata for under $5,000, and I've never once regretted it.

Not only is this car Guinness Record-certified as the world's best-selling two-seat sports car, it's also a popular choice for racers. Mazda claims that on any given weekend, more Miatas are racing than any other single type of car.

— Jake Holmes