Same here... rarely I made money on cars. Once when I sold a F430 which I owned for a week. Other than that I only had to spend.... and always sold in the worst possible moments. All the 911s I sold when they had their lowest low and bought them always brand new on list price.
First time ever I fell I made it right is the SLS and of course that 356 which by now doubled what I paid for.
I guess our problem is, we are listening to our heart and not to the brain when we buy or sell a car. I will try to optimize that in the future.
I 2nd that... When i see how much a 965 is sold now... i almost have to give it away... also my former 993 targa ,same for all the others i owned. Hoping our upcoming boxster spyder will be nicer to my bankaccount.
Even the 996 GT3 i bought an sold last year is now 25k higher on the market :-(
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965 3.3turbo/ 993 targa / 996 cab /997S cab/996 GT3
Audi R8 // Audi A6 3.0 biturbo Quattro/Mini JCW/ 993 cab// boxster spyder on order