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I've said this before, but will do so again. Lol. Why be concerned about how much money "could" be lost years down the road? Unless you are buying a car solely as an investment (and is stored and never driven, plus it's a car that "might" increase in value), you will lose money...it's a given. I guess I see the purchase as a cost, and whatever is recouped later is a bonus. Sure, the bigger the bonus the better, but I paid for the car, I drove the car and I enjoyed the car...all of which were reflected in the initial purchase price; if I sell it later, and get something in return, bonus.
Look at it another way...if you treat yourself to an expensive dinner, should you be concerned that the resale (in say 24 hours) is going to be far, far, far, far less than what you paid? (That's assuming you could even find a buyer. If you do...bonus, I guess).
Another good analogy is going to a casino...I always take what I plan to spend (lose) and if I actually win, bonus. If not, I paid for the experience and enjoyment.
Point is...have fun. Spend what you can afford to lose. Don't worry.
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