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The $5,000 Challenge, spanning-four-decades edition

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A few weeks back on Hemmings Radio, we kicked around the topic of what makes a car collectible. While rarity comes into play, perhaps the biggest single factor is relevance, which explains why once-common cars occasionally become sought-after by those in the hobby. Perhaps they trigger memories of a relative, or of family road trips, or perhaps they’re simply more affordable than other classic cars.

Not every lot in this week’s spanning-four-decades $5,000 Challenge will spur a trip down Memory Lane, but many will. My family had a Comet (a 1962, if I remember correctly), and our milk came delivered in a slightly more modern version of the International for sale here. For the generation that came after me, the K-car was often the family car of choice, and I’m sure plenty of readers have tales of top-down afternoons in a faux woodie Chrysler LeBaron, or the more practical Dodge Aries wagon. Which of these restoration candidates take you back?

1958 Chevrolet Delray

1958 Chevrolet Delray

Someone in the Hemmings Nation grew up taking family road trips in a 1958 Chevrolet Delray sedan, probably hovering on the floorboards for fresh air while Mom, Dad, Uncle Ted and Aunt Betty chain-smoked Kools, Tareytons, Camels and Newports. With just 32,000 miles on this numbers-matching example, chances are it wasn’t the same one that carried you to Yellowstone, or the Grand Canyon, or even down-the-shore, but someone reading this is thinking, “For under four grand, this car needs to be saved.” So are we.

1958 Chevrolet Delray1958 Chevrolet Delray 1958 Chevrolet Delray 1958 Chevrolet Delray

1974 Mercedes-Benz 450 SLC

1974 Mercedes-Benz 450 SLC

Mom and Dad may not have owned a Mercedes-Benz 450 SLC coupe, but perhaps that rich, eccentric uncle that the family only talked about in hushed tones parked one in his garage. While the coupe may not have been as popular as the open-air 450 SL convertible, it was still stuffed full of as much luxury and performance as the Stuttgart automaker could muster, and in 1974, such an automobile would have stickered at $19,450, enough to purchase a Porsche 911 coupe and a Chevrolet Corvette coupe and still get over $3,000 cash back. That makes the $4,500 asking price of this example seem reasonable, assuming that the needed TLC isn’t specialist-only work.

1974 Mercedes-Benz 450 SLC 1974 Mercedes-Benz 450 SLC1974 Mercedes-Benz 450 SLC 1974 Mercedes-Benz 450 SLC

1962 Mercury Comet

1962 Mercury Comet

Used Comets once filled the driveways of suburban America, often purchased for Mom and then handed down through the family to a chain of new drivers. Somewhere along the line, this example fell into enthusiast hands, and the original inline-six was pulled to shoehorn in a 289 V-8 and a four-speed Toploader transmission. That should make it fun to drive, but the car will need some sorting, new floors, interior work and paint to make it a daily driver. Think of the $5,000 asking price as a down payment on restoration training that will include welding, paint and upholstery practice.

1962 Mercury Comet1962 Mercury Comet 1962 Mercury Comet  1962 Mercury Comet

1950 International Metro Milk Van

1950 International

Vans like this once prowled the early morning streets of suburban America, delivering milk, dairy products and bread to a slumbering populace. Today, they make great rolling billboards for small businesses, or even semi-practical toy haulers (try fitting a pair of muddy dirt bikes in the back of an SUV or minivan). This 1950 International is in rough shape, but it’s nowhere near too far gone to save. Spend the $4,000 asking price, get it running and paint it, and perhaps you can even launch a crazy new kind of business, like delivering dairy products to sleeping suburbanites.

1950 International Metro 1950 International Metro 1950 International Metro 1950 International Metro

1985 Chrysler LeBaron convertible

1985 Chrysler LeBaron

At some point in the not-too-distant future, a Chrysler K-car convertible will cross the auction stage and hammer for a positively jaw-dropping price. Why? Even drop-top examples were intended to be disposable cars, driven until the cost of upkeep no longer made sense, then traded in on the latest compact-minivan-crossover-utility-pod, meaning that few K-cars survived into the 21st century. More significantly, these were the family cars for a generation that’s only now earning the kind of money needed to enter the collector car hobby. Combine low availability with increasing demand, and the net result is a jump in pricing. Will this 1985 Chrysler LeBaron ever be a six-figure car? Probably not, but there’s a good chance that, if preserved, it will be worth more than the $4,500 asking price in the coming years.

1985 Chrysler LeBaron1985 Chrysler LeBaron1985 Chrysler LeBaron 1985 Chrysler LeBaron