For reasons I can’t explain, I have always had this dream of living an idyllic life in a small cottage that is perched atop a cliff overlooking the open sea.

The residents around these parts are sparse, as are the clouds in the sky all year round. The nearby township is quite some distance away, accessible through roads that snake along the coastline, with the seaside to one side and countryside to the other, where the only rush to be felt is that of the wind through your hair. It is my sort of road. It’s the sort of road that can only be made right by being behind the wheel of a classic roadster, something like a Mercedes-Benz 280SL ‘Pagoda’.

To me, the Pagoda epitomises the SL lineage. Its clean lines and shape like a French Riviera cruiser lend it a lean and athletic appearance that certainly matches its “Sportlich-Leicht” moniker; an aesthetic that was lost in subsequent generations.

It is the sort of car that I could see myself clocking a million miles on the odometer, then turn it around and clock another million for good measure, and since it was from a time before the malaise of Chrysler, it is almost certain to do another million without breaking a hip.

For much of my youth, the Pagoda was an ambitious goal. It was an expensive car, but still well within the reach of most salarymen at some point in their lives. Now, however, it’s well beyond even my wildest dreams.

The end of the dream for me started some time before the 2010s. It was right around the time when the prosperous baby boomer generation was experiencing their mid-life crisis.

Flushed with cash, they started to covert the cars of their young adult lives, either to realise a promise they made to their younger selves or they had come to the realisation that the late-1990s had altered the course of car development as newer cars were bogged down with ever-increasing regulation-satisfying complication and bulk, sounding the death knell of the beautiful, mechanical simplicity of cars of yesteryear.

Either way, classic cars began to quickly climb in value, which was further buoyed when affluent collectors figured that any profit made off their cars couldn’t be taxed as capital gains because who has ever heard of someone making money from an old jalopy?

During the mid-1970s cars like the Ferrari 250GT SWB California Spyder – and by in large its 250-series kin – were going for less than USD20,000 for a Concours worthy example. Now, you’d be lucky if you can pick one up for less than a thousand times that amount.

Back then an old Ferrari was seen as an old car, a car past its prime and newer cars will have more power, more features, and generally more of everything that made it great. But as the world changed to be more mindful of what comes out of a car’s tailpipe and what happens when a driver’s skill runs out around the turn of the 21st century, cars had to change too.

Humans, who are anything if not obstinate, started to pine for the simpler, romanticised days, when sex was safe and driving was dangerous, and what was once a cottage industry supported by enthusiasts began to burgeon into a multi-million dollar industry with car makers wielding their enormous resources to capitalize on it and reap the generous amounts of goodwill it generates.

An entirely new market was born and it was catered to keep these classic cars on the road, not to be strictly driven mind you, but just fit enough to pass road-legal regulations, so that it doesn’t rack up too many dollar-destroying mileage.

And that is the crux of the issue. While I swore never to talk about resale values exactly a week ago, I have to raise that forbidden subject for this matter alone.

Resale values are meaningless when it comes to driving a new car as all cars will depreciate no matter what you do to it. So you might as well enjoy the fruits of your labour with some proper ‘last days of Rome’ hedonism.

In the classic car game, however, driving it becomes a game of diminishing returns. As you drive along there will be a nagging notion in your head of not how much this is going to cost you, but how much you are losing out on, which is somewhat worse.

Long before collectors started catapulting values, the resale values of classic cars weren’t that big of a deal as they often exchange hands for around the same price amongst enthusiasts. Classic car motoring used to be the sign of a true motoring enthusiast, forgoing decades of progress in efficiency, safety, and comfort, to recapture the spirit of a bygone era. To live the dream in its purest form, free from any pretentiousness or social expectations. Making huge profits from your classic car off a fellow enthusiast was something of a taboo.

Today, the classic car scene has become a craze that has driven out those with a passion for driving and attracted cash-rich investors looking to keep their money from the tax man, with whole industries asking top dollar to keep their ‘investment’ in ship-shape. Sure it has guaranteed the continued existence of classic cars, no matter how temperamental it can be, but now at a hefty financial cost.

Now there are some true heroes out there who have the luck of taking the covers off a classic car and give it a really good hiding on the open road or take it classic car racing. Those folks are worth saluting and lauded, but let’s face it, there are far more folks out there willing to plop a few more grand over the estimated value of a garage queen classic than there are those willing to drive as it should be driven. And besides classic car racing is just some really well-heeled enthusiasts who have the luxury of indulging in a multi-million dollar LARP, some of whom are participating in an effort to add more prestige to their cars than actually living out a passion for the podium, which defeats the purpose of the entire venture.

Ironically, despite the democratisation of cars experienced during the Baby Boomer generation, classic motoring today is quickly returning back to its pre-war era, becoming the plaything and the symbol of the wealthy and the aristocracy once again.

As it stands now, for the price of a Pagoda SL I could buy a brand new SL400 with cash, heck, or even stretch for a V8 SL500 by the time this piece is finished. By the rate values are going, it seems that the classic Mercedes-Benz sitting on the fantasy front porch of my fantasy sun-soaked beachfront property on its own fantasy countryside is the only part that I find hard to believe.

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