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The $5,000 Challenge, Valentine’s Day edition

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What is it that prompts automotive attraction? Why do some of us favor small cars over large cars, or station wagons over coupes, or four-doors over two? Is it genetics? Is it our experience early in life? Is it Cupid, shooting us with a metaphorical gasoline-dipped arrow at a specific point in time?

That’s the beauty of the old-car hobby, and to borrow the timeless used-car-salesman’s creed, there truly is a p(ass)enger for every seat. This time around, the $5,000 Challenge presents an interesting mix of choices, conveniently just in time for Valentine’s Day. If you’re on the receiving end of the gift-giving process, feel free to forward this to your significant other, or, perhaps, print a copy and circle the object of your desire in red. In the end, all of these four-wheel gifts will last longer than a box of chocolates, and they’re healthier as well.


1963 Ford Thunderbird coupe

1963 Ford Thunderbird coupe

Introduced in 1961, the third-generation Ford Thunderbird–often referred to as the “Bullet Bird” for its pointed-nose styling–delivered a unique blend of performance, luxury, and jet-age design. Today, this generation of Thunderbird often represents an affordable entry into the collector car hobby, and this example is no exception to the rule. The interior appears to be in reasonable condition, the paint shiny (with a single bubble of rust to address), and per the seller’s description, all accessories were functional the last time the car ran. Which brings us to the bad news part: while this ‘Bird won’t require significant restoration, it will require a new 390 V-8 to replace the one gone missing beneath the hood. Think of this as an opportunity instead of a drawback, since the buyer can now add as much horsepower as the budget allows. The asking price? $4,995.

1963 Ford Thunderbird coupe 1963 Ford Thunderbird coupe 1963 Ford Thunderbird coupe 1963 Ford Thunderbird coupe


1948 Chevrolet Stylemaster Business Coupe

1948 Chevrolet Stylemaster business coupe

When civilian automobile manufacturing resumed at the close of WWII, automakers had little choice but to restart production of prewar models, often with a simple design refresh. Introduced in 1946, Chevrolet’s low-cost Stylemaster series looked a lot like the 1942 Chevrolet Master Deluxe, but those lucky enough to procure a new car the year after WWII ended wouldn’t have cared. The Stylemaster series remained in production through the 1948 model year, making this two-tone Stylemaster Business Coupe a final-year example. Per the seller’s description, most of the body work has been done, though interior and trim work still need to be finished. There are chrome bits and glass pieces missing,  but this, too, is a positive, giving the next owner a legitimate reason to attend Carlisle, Hershey, Turlock, Charlotte, Portland and other such swap meets in the coming year. Assuming the six and three-speed manual transmission are operational, it might not take that much to get this postwar Chevy back on the road. The asking price? $2,500.

1948 Chevrolet Stylemaster business coupe 1948 Chevrolet Stylemaster business coupe 1948 Chevrolet Stylemaster business coupe 1948 Chevrolet Stylemaster business coupe


1962 Chrysler 300

1962 Chrysler 300 hardtop sedan

In 1962, Chrysler’s high-performance 300 series added a new branch to the family tree. To supplement the highest-output 300H “Letter Series” model, the automaker debuted a range of 300 Sport Series cars that included coupe, convertible and four-door hardtop versions. Visually, the lower-priced 300 Sport Series cars looked a lot like the 300H, and could be configured with many of the letter car’s options, which didn’t sit well with prestige buyers: Just 570 300H models were sold in 1962, compared to 1,617 300Gs sold in 1961. Letter cars are approaching unobtanium prices, but this 300 Sport Series four-door hardtop is (relatively) affordable at our $5,000 cap. It isn’t exactly a driver, and from the pictures it appears to need a new interior and some replacement sheetmetal, but for the buyer with the right restoration skills this could make an interesting project.

1962 Chrysler 300 hardtop sedan 1962 Chrysler 300 hardtop sedan 1962 Chrysler 300 hardtop sedan 1962 Chrysler 300 hardtop sedan


1947 Studebaker M16-28 Series wrecker

1947 Studebaker M16-28 wrecker

Studebaker’s M Series trucks were produced from November 1940 through March 1948, and were available in a variety of configurations and capacities. The stoutest version, the M16, came with either a 1.5-ton or 2-ton capacity, and was equipped with the higher-output Commander six-cylinder engine. The M16 was also available in three wheelbase lengths, ranging from 128-inches (the M16-28) to 152-inches (the M16-52) to 195-inches (the M16-95). This short-wheelbase M16 wrecker will need a bit of mechanical and interior work to put back on the road, but none of the rust appears to be serious. Those with a passion for patina could leave the exterior as-is, though we can’t help but wonder just how spectacular this rig would look with a full-on restoration. The asking price?  $5,000.

1947 Studebaker M16-28 wrecker 1947 Studebaker M16-28 wrecker 1947 Studebaker M16-28 wrecker 1947 Studebaker M16-28 wrecker


1988 Porsche 924S

1988 Porsche 924S

Porsche’s transaxle models – the 924, 944, 968 and 928 – have climbed in value in recent years, but the 924 still represents an affordable starting point to Porsche ownership. This desirable final-year 924S comes with the 944’s 2.5-liter four-cylinder engine, rated at the full 158 horsepower instead of slightly detuned as in the 1986-’87 models. In a drag race, the lower-priced (and lighter) 924S was reportedly faster than its more expensive 944 stable mate, though it isn’t likely that Porsche ever sold a 924 for its quarter-mile performance. From the seller’s description, this sounds like a driver-quality example that wouldn’t take much to turn into a show car. It needs A/C work, a wiper motor for the rear window, and a bit of sunroof repair, but none of these details should prevent the next owner from enjoying a fun car on twisty roads until the repairs can be carried out. The asking price? $4,000.

1988 Porsche 924S 1988 Porsche 924S 1988 Porsche 924S 1988 Porsche 924S