The 5 Dream Cars You’ll Regret Owning but Still Secretly Want

Whether it’s a case of being blinded by the beauty of the design, enthralled by the vehicle’s capabilities, or simply blown away by its potential for performance, there are a surprising number of truly “heartbreaking” cars out there that we all still want to own. Here are five of the most intriguing offenders that generate pulse-quickening passion and code-blue palpitations even as they ask us to overlook their pitfalls before parking one in the garage.

1993-1995 Mazda RX-7 FD

Why we love it: Has Japan ever produced a more gorgeous car? The final-generation FD RX-7’s flowing sheetmetal and pop-up headlights represent a high bar for ’90s styling that still manages to look contemporary more than 30 years after its debut. Then there’s the fact that this lightweight (less than 3,000 pounds) sport coupe is beautifully balanced and features a sequentially turbocharged Wankel rotary engine that nears 8,000 rpm at full throttle in search of its 255 horsepower and 217 lb-ft of torque.

There’s truly nothing like it on the modern market, and it represents that brief sliver of time when Japan’s bubble economy was pushing a dizzying array of high-tech, near-supercars onto the American market at a breakneck pace.

Why it will break our hearts: About that rotary engine. You see, there’s nothing inherently wrong with the RX-7’s drivetrain, it’s just that swapping pistons for a Wankel’s spinning rotors pushes you through the looking glass when it comes to this Mazda’s ownership experience. Say goodbye to nearly everything you know about maintaining a traditional internal combustion engine, and say hello to carefully observed warmup routines (up to 10 minutes of idle to get up to temp, then a few minutes of easy driving after a cold start), to oil consumption (a ‘feature’ designed into every rotary engine), to apex seal replacement (a non-trivial job), and to heat damage suffered by every plastic or rubber tube, hose, or clamp in the engine bay primarily due to the turbo system.

Then, of course, there are the must-do reliability mods, like replacing the pre-cat, dumping the ready-to-crack air separation tank before it bathes the engine in coolant, and swapping in an all-aluminum radiator for the original one with the brittle plastic end tanks. None of the above is terminal, but you’ll be lucky to find a rotary expert in your area without a three-year waiting list. This RX-7 is perhaps the only car in this story that requires you to adopt an entirely new lifestyle just to support and feed it in the manner it requires.

1995-1999 Ferrari F355

Why we love it: The Ferrari F355 was the last of Maranello’s Italo-wedge monsters, a car whose look is so iconic that seeing one on the street instantly evokes images of Michael Bay movie explosions, the model’s own bespoke racing series, and the fiendishly difficult F355 Challenge video game the latter inspired. Featuring a mid-mounted, 3.5-liter V-8 engine good for 375 horsepower, the F355 also debuted Ferrari’s “F1” automated manual gearbox that promised to pair quick, direct shifting at speed with hands-off operation when cruising.

Ferrari’s answer to the velvet-gloved slap of the Acura NSX and a substantial improvement on the less loved 348 that came before it, the F355 shifted better, was better suited to daily driving, and offered exceptional performance. Its classic look has yet to be bettered by any modern F-car.

Why it will break our hearts: The F355 is in many ways the last of Ferrari’s old-school supercars, especially from a maintenance perspective. What does this mean for owners? Be prepared to splash out big bucks for engine-out service on a semi-regular basis, with the timing belt due every three years (potentially setting you back well over $10,000). And that’s if nothing goes wrong, as problems with the F1 gearbox’s electrohydraulic system are notoriously finicky and expensive to deal with, and earlier cars feature valve guide wear problems that can cost just as much to fix as a timing belt install. Oh, and then there are the exhaust headers with nearly a 100 percent fail rate, which will pay for a set of braces for your Ferrari mechanic’s kid.

Let’s be clear: There’s nothing about the F355 (aside from its trick automated gearbox) that’s dramatically more expensive to deal with than the mid-engine Ferraris that came before it. Its replacement, however—the Ferrari 360—pushed the brand into the modern era with a design that keeps the engine inside the car when tackling various maintenance tasks, which cut operating costs by as much as 50 percent. The tragedy of the F355 is that one of Ferrari’s most beautiful designs hails from a period that just misses the cusp of an ownership experience that doesn’t require a second mortgage.

1999-2004 Land Rover Discovery II

Why we love it: If ever there were a classic SUV designed specifically to meet the needs of the current overlanding craze, it’s the Land Rover Discovery II. With a long wheelbase intended to accommodate three rows of seating, there’s a ton of internal space to transform into whatever sleeping/cooking/living arrangement might be required, m