12 Mar 2025 3 min read

Vintage Horsepower: Why Driving a Classic Beats Leasing a New M5

By Thomas Crown III – March 15, 2025

If your automotive strategy revolves around leasing the latest German super-sedan to impress strangers at the valet stand, consider this a financial—and aesthetic—intervention. A 2025 BMW M5 tipping the scales at a porky 7,000 pounds is as subtle as a neon sign flashing "Insecure Rich Guy," while leasing a Lexus GX 550 loudly proclaims you couldn't get approved to finance a G-Wagen. It’s high time you embraced vintage horsepower.

Classics aren't about nostalgia or quirky collector eccentricities; they're strategic investment plays. Forget the leasing hamster wheel—where your shiny new sedan depreciates faster than your accountant can track. Vintage cars, carefully selected, appreciate steadily, making them your portfolio’s—and your driveway’s—most compelling allies.

Depreciation is for Suckers

The instant your leased BMW hits pavement outside the dealership, its market value plummets quicker than your crypto holdings during an Elon Musk tweetstorm. By contrast, a wisely selected classic—say an air-cooled Porsche 911 or a Mercedes 560SL—quietly appreciates, padding your net worth as effortlessly as your ego.

Timeless Style Beats Temporary Flash

Paul Newman’s Rolex Daytona isn’t legendary merely for timekeeping—it’s legendary because Newman wore it. Similarly, the BMW E39 M5 isn’t revered purely for horsepower; it symbolizes engineering excellence, discreet sophistication, and the end of the analog automotive era. Today’s leased M5, burdened with screens, nanny tech, and sterile performance, resembles a soulless appliance.

Privacy in the Age of Digital Intrusion

Modern cars are mobile spyware. Elon’s Tesla, armed with microphones, GPS trackers, and cloud-connected software, can remotely lock or brick itself at whim. (Or potentially worse—remember Michael Hastings?) A vintage analog classic inherently respects your privacy by lacking any technological capacity for betrayal. No intrusive GPS, no sneaky software updates, no algorithms eavesdropping—just unfiltered automotive freedom.

Maintenance: The Strategic Advantage of Having “A Guy”

Critics raise the red flag: “Aren't classics maintenance nightmares?” Yes, but only when bought impulsively or without guidance. Savvy classic car enthusiasts—like GildedLore readers—understand every classic needs “a guy”—a trustworthy mechanic. Developing relationships with marque specialists transforms maintenance from a dreaded chore into strategic advantage. Unlike new BMWs mandating dealership servitude, your vintage Mercedes requires only Hans, who values craftsmanship over billing cycles and upselling.

Seven Classics That Appreciate Even as You Drive

1. BMW E39 M5 (1999-2003)

394 horsepower, naturally aspirated 4.9-liter V8 (S62 engine)
Renowned for its superb driving dynamics and considered BMW’s pinnacle of analog luxury-performance sedans.
Current market: $25,000–$45,000

2. Porsche 911 (993 Generation, 1995-1998)

272-horsepower Carrera up to 450-horsepower Turbo S
Celebrated as the last air-cooled 911, offering legendary reliability and iconic design.
Values range from $60,000–$200,000+

3. Cadillac CTS-V Wagon (2011-2014)

Supercharged 6.2-liter V8 with 556 horsepower
Rare combination of luxury, practicality, and muscle, with manual variants commanding premium prices.
Prices currently range from $50,000–$70,000

4. Acura NSX (First Generation, 1990-2005)

Mid-engine 3.0-liter V6, 270 horsepower
Known for challenging European supercars with superior reliability, craftsmanship, and iconic handling dynamics.
Values climbing steadily; $60,000–$100,000

5. BMW E30 M3 (1987-1991)

High-revving 2.3-liter inline-four, 192 horsepower
Legendary motorsport heritage and iconic boxy styling fueling rapid value appreciation.
Rapid appreciation; $70,000–$120,000

6. Toyota Supra MKIV (1993-1998)

Twin-turbo inline-six (2JZ-GTE), 320 horsepower
Pop-culture legend boosted by reliability, modifiability, and an enthusiastic fanbase.
Values surging, currently $50,000–$100,000+

7. Mercedes-Benz R107 560SL (1986-1989)

Elegant 227-horsepower 5.6-liter V8 convertible with timeless design.
Ideal sunbelt cruiser, famed for build quality, classic elegance, and reliable luxury. Manual tops standard; no factory power tops but easy to operate and maintain.
Appreciating steadily; $25,000–$50,000

Liquidating Your Classics

If your tastes shift, classics offer effortless exits through respected platforms like Bring a Trailer, Cars and Bids, Bonhams, or RM Sotheby’s. Unlike volatile stock investments, your classic’s value won’t evaporate due to corporate scandals or Twitter storms.

Every Classic Has a Story (Unlike Your Neighbor’s Tesla)

Cars, unlike municipal bonds or ETFs, tell stories. Arriving at a dinner party in your leased Audi states merely: "I have credit." A Jaguar E-Type or air-cooled 911 generates intrigue and instant conversation.

Trade leasing blandness for the cultural enrichment of vintage ownership. Real wealth isn’t mere numerical accumulation—it’s about living exceptionally, artfully, authentically. Embrace vintage horsepower, and your future self will thank you.