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I'm in the same boat. The black book trade price for my car said it ranged from $9800 to $12,900. I have 25k invested thus far. Of course, I'd never trade a car this old for a new or newer boxster... I'd sell it to a private party.
I don't think I will ever sell my car unless I come into a sizeable inheritance and buying a new or newer one is just a simple decision for me and the loss isn't painful.
So a sunk loss of my own will only be experienced after many, many more years of enjoyment!
I absolutely love driving my car. It's great fun and continues to be a dream come true for me. My buddy with the 944 feels the same way, so we don't have bigger dreams like some do (trade up to a turbo, a GT, Ferrari, whatever).
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