Prices may be coming up, but this doesn't count inflation and value of dollar. For example, I bought my Boxster in 2009 for (what I thought was a steal) $15,000 (as an FYI, it's an 01 that had about 32,000 mi then). I figure that with the TLC, upgrades and low mileage I've put on, if I could find the right buyer I *might* get $15,000 (not that I plan to sell). Sound like a pretty good deal, right?
But let's figure in adjusted dollars; according to the Bureau of Labor Statistics consumer price index, prices in 2018 are 17.46% higher than prices in 2009. The dollar experienced an average inflation rate of 1.80% per year. In other words, $15,000 in 2009 is equivalent in purchasing power to $17,618.57 in 2018, a difference of $2,618.57 over 9 years. Now I suppose that I need to figure in "major repairs" (IMS upgrade, water pump, etc) and I'm quickly approaching $25,000 in adjusted dollars....still excluding regular maintenance costs. My point is that even if I were to sell and got the magical $15,000 I originally paid, I've still lost about $15,000.
This is why I don't fixate on resale...price is subjective, and unless you flip almost immediately, you are going to lose money. Actually, I rather reject the term "lose money" as the way I see it, I just paid for a whole lot of fun. If you look at it that way, it's pretty cheap, and money well spent.
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