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As a teenager, my bedroom walls were covered with posters of tricked-out Porsches and lowered Ferraris. I fantasized about the modifications I would perform to make them even better: shark-mouthed brake ducts, snaking titanium exhaust headers and high-lift camshafts. Only later, as a grown man with a mortgage, did I realize what the ultimate car accessory really is: a parking spot.

I thought of this recently as I passed a beautiful Porsche 911 that sits on the street near Christie Pits each day, exposed to wind, rain, and the despoilations of every passing seagull. This is the kind of car I dreamed of when I was a kid – but in my dreams, parking was never a problem.

In real life, it is – especially if you live in the big city. As I've learned through brutal experience, there is an inverse relationship between property values and parking satisfaction. In Toronto, it's easy to spend more than $1-million on a home that doesn't have a parking space, let alone a garage. This explains why you see so many dream cars parked out on the street as if they were beater Hyundais.

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There are no easy answers to the problem of parking in a major city, and money only takes you so far. Jerry Seinfeld spent five years and several million building a garage in Manhattan, yet it holds only five cars. My friend Dan has a castle of a house in Rosedale with a custom library, wine cellar and a kitchen that Martha Stewart would die for. But he has only a single-car garage. Dan may have climbed to the top of the corporate ladder, but the poorest hillbilly in the Ozarks has better parking.

Parking is the dream killer. This first dawned on me back in the 1970s, when I bought a BMW 2002 Tii that needed an engine rebuild. I worked as a mechanic back then, so the engine work wasn't a problem. Finding a place to do it was. The shop where I worked didn't have space for personal projects, and I lived in a house with four roommates and a single parking spot – a short, rough gravel driveway that was overhung by a giant maple tree. By the time the engine was done, I'd spent two weeks out there, deluged by rain and maple seedpods that spun down around me like thousands of tiny helicopters.

When the BMW was finished, I had nowhere to park but the street (one of my roommates had dibs on the driveway). This arrangement was not ideal. The bumpers of my newly rebuilt BMW were soon scarred by careless parkers, and a drunk relieved himself on it one night, causing a faint urine odour that proved impossible to fully exorcise.

Not long after that, I foolishly carried out a meticulous restoration of a VW Beetle, putting months of effort into the bodywork. Each panel was carefully straightened, block sanded and painted, yielding a perfect, mirror-like finish. Then I parked it on the street (the only place available to me at the time) and hoped for the best. A month later, a tow truck backed into it.

By the 1990s, I was a young dad, living with my wife and kids in downtown Toronto, where parking continued to put a damper on my automotive dreams. Our car was a base-model Honda Civic, and we lived in a two-storey downtown flat with a weed-infested parking pad out front. When a friend offered to sell me his beautiful Caterham Seven (a tiny English sports car with a top that resembles an army poncho held up by sticks) I was ready to write the cheque. But my wife vetoed the deal, pointing out that a garage was a prerequisite for owning a car without an actual, weatherproof roof. When I concocted a contingency plan that involved swaddling the Caterham in tarpaulins that would have to be removed and reinstalled for every drive, my wife rolled her eyes and moved on.

And yet, in the breast of a car nut, hope springs eternal. Despite my parking-deprived status, I still entertained delusions of buying an awesome sports car. For a while, I sketched designs for a collapsible steel protective frame that could be erected around my car when it was parked.

Finally, I bit the bullet and bought a house, even though it wiped out my sports car fund. Naturally, the house came with a garage spurred by my earlier experiences, I refused to look at houses that didn't have one. And yet my parking woes weren't over. Home repair projects and family storage often took up part of the garage (and sometimes all of it). Our cars had to go outside, where they were at the mercy of the elements and Toronto's ever-buzzing green hornets, who issue 2.8 million parking tickets a year (ticket prices start at $30 and, if you don't get a few each year, you probably don't own a car).

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Overcoming the limitations of big city parking calls for ingenuity and, unfortunately, money. One of my friends recently installed a second car lift in his garage, which allows him to park four cars instead of two. I am trying to save up the cash to tear down my leaking garage to build a new one, complete with a car hoist. In the meantime, I finally have my sports car (which I keep parked in the front left corner of the garage so as to avoid the worst of the roof leaks).

Living in a crowded big city with little parking options such as Toronto means that many beloved cars spent too much time outside exposed to the elements. The Globe and Mail Peter Cheney The Globe and Mail

And despite the leaks and the intrusions of family projects on my hard-won garage space, I count my vehicular blessings. Almost every day, I pass awesome cars that are parked out on the street like kings without castles. There's the grey Porsche over by Christie, its polish dimming in the sun. There's a nice, copper-colored Dodge Challenger down off College. It has custom plates, and it's almost always freshly waxed. Leaves fall on it every October, and in the winter, it gets buried when the snowplow goes by.

That's the life of the big-city car buff – all dressed up, but no place to park.

For more from Peter Cheney, go to (No login required!)

Twitter: @cheneydrive

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