1969 Jaguar XKE Series II

Ever see one on the street? No? Sadly, the world's most beautiful car is also one of its least durable. Even those who own and love them describe them thus: "XK-Es used electronics from the dark prince, overheated even in Alaska and their bodies turned to Swiss cheese within two years of purchase."

But if you had the mad courage to own an XKE, this is the one to get. Many of the shortcomings of the first series were overcome, including an improved transmission, cooling system and seats. On the other hand, the Series II lacked the supercool glass-hooded headlights of the earlier cars. In 1971, Jaguar introduced the Series III, with the impressive but ill-fated V-12. That car found a whole new set of problems to make "XKE" synonymous with "unreliable".

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1960 Ferrari 250 GT Coupé Pinin Farina (Chevy Powered)

You can pick up one of these in restored condition for around $700,000. So what is this Ferrari even doing on the street at the Greenwood Car Show? Someone might breathe on it! Well I don't know how much this car is worth, because it's been repowered with a Chevy V-8. I'm informed that "dozens" of old Ferraris received this treatment back in the day. Certainly its value is still way up in the six figures.

From drive-my.com: "The concept of ditching Ferrari’s glorious V12 for V8 iron may be hard to digest in today’s world, when ‘matching numbers’ authenticity is all-important. Back in the 1950s and ’60s, hot-rod culture was second nature to kids in America, when virtual wrecks could be ‘chopped’ and tuned to become the fastest things on the road. The most straightforward way of achieving that was by transplanting a bigger-capacity engine from an American car. When your Ferrari engine went terminal, or couldn’t easily be fixed, the pragmatic move was to whip out the V12 and install a Chevrolet or Ford unit. Hey presto, your gorgeous Italian stallion was up and running again – at a stroke, going from 3.0 litres to 5.7 litres, with 100 extra horsepower to boot. The Chevy’s advantage was its compact – ‘small block’ – size and short stroke, which reduced piston speed at high revs. It was reliable, too."

Ferrari built 353 copies of this car between 1958 and 1960. That's a lot of cars by old-time Ferrari standards. The previous 250 GT coupe sold 138 copies between 1955 and 1958.

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1966 Triumph TR4

"Most machines that have been on and off the road for the better part of 50 years are going to have some issues. The TR4A was simply built with more of them to potentially address." That's the polite way that Hemmings describes the pitfalls of owning a Triumph. This is a fun car; sportier than an MG and a lot cheaper and simpler than a Jaguar. If you can get past: (1) you can practically hear it rusting, (2) it takes genius to tune a Triumph's valves and sidedraft carburetors and (3) I don't think even the guys who designed this car understood its electrical system.

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