The subject car is a 1993 Bentley Continental R Coupe. No doubt it’s special. It cost almost $300,000 new, and only a few hundred were built. The model was created in order to emphasize Bentley’s sporting heritage, and to set it apart from its sister marque, Rolls Royce.

It took a new body, a turbocharged engine, and a sporty suspension to create sort of a banker’s hot rod: super fast and super thirsty; a big car but not particularly roomy inside; hard to park, but too nice to entrust to a parking lot attendant.

First thought about $100,000 used cars – they’re probably not everyday cars.
This Bentley is fast – brutal acceleration and a top speed sufficient to use up most of its 170 mph speedometer.

The first Bentley Continental appeared in the early ’50s as a fastback two-door. Some claim its shape was inspired by the Buick and Cadillac sedan-ettes of the late ’40s, but Bentley aficionados don’t like that idea much.

In any case, the first Continental upheld the Bentley reputation, established with several wins at LeMans in the late 1920s, for effortless high-speed travel. The 1993 model delivers on that issue in spades. And the ’93 is a totally original shape – elegant and restrained, subtly sculptured.

Don’t like the Bentley? How about a Ferrari? Bentleys are dark green, tall and quiet. Ferraris are red, low slung and noisy. They don’t even pretend to be an everyday car, but if you’re an able and keen driver, you’ll love everything you hear, feel and see. At around $100,000, there are plenty to choose from, because every year recently, Ferrari has sold around 1000 cars in the U.S., many of those in California. (Maybe you’ll buy a Toyota/Honda/Audi/BMW for everyday and a Ferrari for Sundays.)

One difference between $100,000 used cars and normal used cars is that sometimes the value of the former actually increases, whereas the average car loses 50 percent in three years. Don’t bother using that fact as justification though – repairs may skewer your cost projections.

Sometimes you can’t even pretend. A friend of mine bought a car in this price range that he’ll probably never drive. It’s a mid-’60s Dodge Challenger, with a new Viper V-10 motor – a totally useless, beautiful, exercise in excess and impracticality. Let’s hope another fantasy-driven collector appears someday and buys it.

A big factor driving values is the eligibility of a particular car for entry into racing or driving events, or car shows. Rarity and race history can be powerful influences. An early Mustang suitable for local old car shows may command $20,000, but the Ford GT40s that won at LeMans in the same time period can easily bring seven figures!

Collector car auctions, like the much-televised Barrett-Jackson extravaganza in Scottsdale in January, or the Christie’s/Sotheby’s/RM/Blackhawk events in August on the Monterey Peninsula, have sold many $100,000-plus cars in recent years. Two that come to mind are a 1932 Alfa Romeo 8c, at nearly $2 million, and a 1957 Chevrolet Corvette at $240,000!

It’s a somewhat risky way to buy a hobby car, because you can’t drive it first. And the transaction costs are high, with buyers’ premiums ranging up to 17.5 percent, on top of the commission the seller pays. But the auction excitement seems to be a strong attraction to bidders.

Some cars that might be qualified to command six figure prices haven’t, possibly because they’re too common (although being common hasn’t depressed the value of certain Fords and Chevrolets).

One of my favorite high-value used cars – albeit something of a bargain at $25,000-75,000 – is any well-preserved Cadillac convertible built between 1936 and 1970. Two generations of Americans, and people from many other countries, regarded these cars as the top symbols of automotive prestige.

They were damn good cars too, arguably the equal of the best cars produced anywhere. As art objects, they portray an entire culture. One well-know artist, Nicola Wood, an Englishwoman working in Los Angeles, exhibits paintings featuring Cadillac convertibles in various fantasy settings.

In common with other high value cars, these Cadillacs aren’t much good as practical transportation, and they cost the earth to maintain. Those maintenance costs, however, can be one of the charms of ownership. Why? Because once you find "your" mechanic, you’ve joined another secret society – the circle of customers who think this guy walks on water, no matter how high the repair bills.

Here’s a comparison between ordinary cars and $100,000 cars:

Practicality, Usefulness – of almost no importance in the $100,000 used car. Highly important in the normal car.

Reliability – sometimes, the worse the better. Great stories to tell; great puzzles to be solved in the repair shop. New car: If the CD malfunctions, even under the lifetime warranty, swear off that brand and buy a different make next time.

Purchase Price – What the hell – it’s only $15,000 more than I expected, but it’s for my dream, right? New car: Hard bargaining – $299 a month lease or I’ll walk out.

Are you tempted? If so, here are a few words of advice. First, figure out what you like. Forget price appreciation. If you haven’t made your money in some other way, an old car won’t rescue you. Second, shop around. You’ll learn a lot, and at least half the fun is the shopping. Third, buy the best car of your type that you can find. In the end, the best (and probably most expensive) will likely cost the least overall.

If you do jump in, be forewarned. One car probably won’t be enough. Life will become a constant search for balance, with time, money and space the competing factors. Be prepared to lose – if you have a surplus of any one of these factors, it will lead to a shortfall in one or both of the others.