Joe turns 40 next year. He clearly has a predilection for fun, stylish and maybe even unconventional choices, which is why he has a 2016 Cadillac ATS Coupe. But he turns that lease in next winter, and now he’s looking for his last car—ever. What car should he buy?

Welcome to What Car Should You Buy?, a new Jalopnik feature where we give real people real advice about buying cars. Do you want us to help you find a car? Send us an email with “What Car Should You Buy?” in the subject.

Most of us end up owning many, many cars in our lifetimes. Few of us get to be as fortunate—or crazy—as someone like Jason Torchinsky, who has owned his Beetle since he was 18. That’s because at the end of the day most people depend on a car to get around, and doing that in an older car usually requires time, commitment and wrenching skills.

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But now, thanks to a change of circumstances, Joe has a chance to own that long-term daily-driver, and he wants something classic: a childhood fantasy, he says.

Here’s what he’s after:

I’ve grown up in LA and until recently, have always commuted. Now, I work 7 miles from home and pedal a few days a week. This will be my near daily driver, but more importantly, the chance to live out childhood fantasy. My budget is $20-25K because I’d like to find something that is relatively classic, in fairly good shape and that after 3-5 years of investment of time, effort and a max of $5K a year will still feel like a good idea.

I have my own garage and tools, I grew up maintaining my own cars until I started buying and leasing new vehicles with manufacturer warranties.

I’d love it to be a convertible. Again childhood fantasy to take a weekend cruise along the coast and listen to Randy Newman sing “I Love LA”. I know I can achieve the goal of Mustang at the top of my budget, but I get the sense that I’ll be pedaling or sharing my wife’s Forrester more than a few times in the first year. I could go with a Corvair for about half my budget and enjoy the (pause)… never mind. Except that I’d need to lengthen my garage, I’d love a classic Cadillac.

So there’s my conundrum. I can finally afford to live out my childhood motoring dreams, but I’m concerned about losing the joy of it should I choose the wrong car. I’m happy to give up the security of a bumper to bumper warranty and a dealer rental, for late nights and weekend trips to AutoZone. I feel like Indiana Jones choosing the Grail. Please help me choose wisely.

Quick Facts:

Budget: $20,000 to $25,000

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Daily Driver? Yes, with the understanding that there will be times when it’s under repair and he’s biking to work

Average Miles Per-Week: 30-50

Wants: Relatively classic, convertible, probably American

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Doesn’t want: To finance a car, something too expensive to maintain, to sell in a few years and regret the experience


Expert #1: Patrick George, Chief Enabler of Bad Decisions

Joe, you’re in a great position to be a classic car owner now. You don’t have a lengthy commute, you have a healthy option when the car’s out of commission, you have a good budget and you know how to wrench.

One thing that comes to mind for me right away is that no matter what you decide to do, don’t let the fear of regret hold you back. Even the most ill-fated car experiences can turn into good stories, and in the worst case scenario, you’ll pick up some more mechanical skills and a more solid idea of what you want if this purchase doesn’t work out. Find something that speaks to you, go for it and don’t look back.

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I’m also a believer in the idea that the first answer that comes to mind is the right one. You mentioned a classic Mustang, and those are great choices, but... a bit obvious, no? Some might even say basic, unless you’re going for an original Boss 302 or something.

I say buy the Corvair, but I’m clearly biased here. It’s weird, it has a fascinating history, it’s my favorite classic American car, and I have a feeling it will lead you to a ton of great adventures. Here’s a turbo one near you for just $14,500.

Just don’t lift in the corners.

Expert #2: Michael Ballaban, Deputy Chief Inspector, Terrible Ideas Division

Photo: Joe Ross/Flickr

The year is 1981. President Reagan has brought morning to America again. Humanity’s collective cultural output is at its eternal peak, as Kenny Rogers wins the American Music Award for Best Pop/Rock Male Artist, and Barbra Streisand wins the women’s counterpart. Billy Joel, Bob Seger, Olivia Newton-John, and Linda Ronstadt are all runners-up.

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The best car in the world is the 1981 Chevrolet Corvette. It has a four-speed manual and a wheezing, struggling, 190-horsepower 5.7-liter V8. It’s also even better than a convertible, with a T-top roof.

But there’s something about these late C3 Corvettes that make them absolute charmers. They’re a triumph of style, with the epitome of a Coke-bottle shape. They actually can even sound pretty great, too. And since they’re not too fast on paper, you can actually have a blast without getting constantly dinged by the cops.

Grow your hair out and snag this one. It’s got only 33,309 miles on the clock, and it’s in pristine condition for a $22,999 asking price. It doesn’t get any better than this.

Expert #3: David Tracy, No One Is Sure How He’s Still Alive Exactly

Photo: Jeep via Favcars

You say your dream is to cruise along the coast in a convertible listening to Gary Newman. As far as I can see, there’s really only one convertible vehicle that can actually get you to the coast, and that’s a Jeep CJ, my favorite of which is the CJ-7.

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Pop the thing into four-wheel drive and she’ll conquer any sandy beach you want to take on. It’s really one of AMC’s finest products: longer than the CJ-5, so there’s actually room in the back seats, you can get it with the un-killable 258 cubic-inch inline-six engine, and you can get a five-speed manual. What more could you ask for?

You say you’ve got your own garage and tools, and that you’ve got experience wrenching. Well, I can tell you, there are very few vehicles as easy to work on as an old Jeep CJ. Plus, parts are cheap, and the things just don’t lose value. Yes, you definitely need a CJ-7.

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Of course, finding an unmolested one can be a pain in the ass, as everyone seems to want to put huge lift kits and tires on them. But stock and near-stock ones are out there, and they usually go for well below what you’re looking to spend.

Expert #4: Jason Torchinsky, Famous Internet Dipshit

Look, ignore what all these other guys wrote, okay? They mean well, and I like Corvairs, but they’re all wrong. I can say this because I’m the only one here who has done almost exactly what you’re talking about. As you read up top, I’ve had a classic car since I was 18, and I’m older than you are now.

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Ballaban’s ‘Vette is just going to make everyone immediately assume you have chlamydia whenever you pull up anywhere in it, and you don’t need that sort of headache.

The manner of headache you do need are the special, wonderful sort provided by a vintage air-cooled Volkswagen. I know it’s not American, but it’s like a naturalized citizen. I’ve had my ‘73 Beetle since I was in college, and I’ve daily driven that car almost constantly since that time so many decades ago.

I’ve kept that thing going during periods when I was broke, I’ve put money into it when I had it, and I can absolutely say that the dirt-simple mechanicals of an air-cooled VW can be kept going forever. Not trouble-free by any means, but there’s no reason why anything should keep you from getting the car going again until the heat-death of the universe.

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You’re a classier guy than I am, so I think your classic car convertible cruising down the PCH needs would be best served with the classier air-cooled sibling, a Karmann-Ghia.

Same common, well understood VW mechanicals underneath, and on top is a genuinely lovely body. That body is a bit of a liability because it’s all one piece, save for the bits that open, so there’s no bolting on parts in a wreck.

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That’s more expensive, but the smooth look makes it worth it. Besides, you live in LA, which is basically the world capital of vintage VWs. There’s parts and shops and experts all over the place. There’s no rust, either. It’s the ideal place to have an old Ghia.

Look, here’s one (near me, but you can find these out West even easier) in fantastic shape for $17,000. It looks perfect. You’ll love it.