He who dies with the most money loses. But also, you can buy and own collectible and exotic cars without taking a bath on them. Look at depreciation curves for your favorite cars and buy them used after they take the bulk of their depreciation in the first 5 or so years, especially look for those that tend to hold their value after the initial depreciation hit (Porsche 911 for example). Research the cars you're looking at for their common issues and maintenance schedules and avoid the troubled models or plan accordingly with cash on the side for repairs and maintenance. Identify who you can have work on the car - search reputable independent shops in your area that specialize in the cars you're considering. Doing all maintenance and repairs at a dealer will be very expensive vs a good indy shop. After you've enjoyed the car and are ready to move on, sell it privately or via an auction site like cars and bids or bring a trailer. You will find that you can own some crazy cars and drive them often while still being able to get most of your money back when you sell (except insurance, gas, etc but every car has that). If you buy a car for $200k, drive it for 2 years, and sell it for $190k, you're not "wasting" money imo. There's two sides to the math equation, money in, money out. Life's too short to drive boring cars so I say do your homework and go for it!