The Used Cars (and Motorcycle) We’d Buy Right Now for $5,000

Simple thought experiment: you’re given a tax-free $5,000 limit and told to buy a car. Any car. We know what we’d buy — not that we didn’t spend a few hours (okay, all afternoon) debating and competing with each other for the “best” pick. This will be an ongoing series — other spending limits will follow — but why not start with the car we’re all most likely to purchase, perhaps on a whim? Check out our picks below, and please keep us in your thoughts as we annihilate our bank accounts.

1988 Porsche 924S

My dad owned a 1984 924S when he first moved from California to New York, and I wish that he had held on to it. Now is my chance to own one of my own. Yes, it’s in Vermont and likely has a ton of rust problems, but, hey, it’s only $4,000. Tuck it away in the garage and bring it out for the occasional spirited weekend drive. I can finally relive my childhood memories in this car, except this time I’ll be driving. It comes equipped with a 2.5-liter, 158-horsepower inline-four, but for a car this small, that’s plenty to have fun with. — AJ Powell, Assistant Editor

Mileage: 72,900 miles
Original MSRP: $27,215

1972 MG Midget Mk III

This 1972 MG Midget is the perfect example of a classic British Roadster. It’s a lightweight, hilariously underpowered and occasionally reliable little bundle of English design known less for straight-line speed than for superior handling in tight, curvy turns. This particular example is a quirky one. Not only is it finished in a questionable mix of bright green and blue, but it seems to come with a matching canoe that’s far longer than the damn car. It’s relatively rust free and has fully chrome bumpers, the last generation of Midget to do so before the unsightly addition of US spec black plastic bumpers. — Hunter Kelley, Design & Photography Apprentice

Mileage: 6,000 miles (on the rebuilt engine)
Original MSRP: $3,500

1993 Mercedes-Benz 300CE

The W124 chassis from Mercedes was something of a final hurrah for the “over-engineered” Benzes of the ’70s, ’80s and early ’90s, and the 300CE pillar-less coupe might be its greatest iteration. It has an inline-six good for 217 horsepower (when new, anyway), so unlike other boxy Benzes of its ilk, this one actually has enough power to get out of its own way. Further, the engine bay, body and leather interior look incredibly immaculate, making the sub-$5,000 price feel even more like a no-brainer for this classy means of conveyance. — Andrew Connor, Associate Staff Writer

Mileage: 135,900 miles
Original MSRP: $52,500

2000 Jeep Cherokee (XJ) 4WD Sport 4-Door

One might not think that an automotive editor would be car-less, let alone residing in NYC, where owning and managing car logistics is difficult at best. But I’m aaaall about upending expectations. I also daydream constantly about owning an XJ 4×4. A friend in college had one; I remember my dad renting one years before that. It is the SUV missing link — a unibody ute with a supremely torquey and smooth inline-six, beautiful, boxy styling and capable four-wheel-drive. It’s 100 percent practical: everything you need, nothing you don’t. I want one badly, and when I see one in good condition at a price like this, I start thinking very, very dangerous thoughts. — Nick Caruso, Associate Editor

Mileage: 140,312 miles
Original MSRP: $21,415

1971 Ossa Pioneer

It’s slim pickin’s below $5,000. I was tempted by an old NYC yellow taxi and a brown ’81 Jeep Loredo with an interior that looked like the result of someone skinning Paddington Bear. Neither were in that great of condition. Truth is, not much is at this price point — on four wheels. But on two wheels I can get this rad ’71 Ossa Pioneer enduro in near-perfect condition. — Bryan Campbell, Staff Writer

Mileage: 2,527 miles
Original MSRP: ~$1,200

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