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Unless the tweaks are bolt-on and easy take-off, like upgrading to litronics, I doubt you'll ever get your money back out.
Regarding depreciation, I suspect everything post 993 is going to face much greater depreciation. There will be the exceptions like GT2s and GT3s (possibly Boxster Spyders and Cayman Rs for their Club Sport-like design) that will hold their value pretty well.
The 996tt are kind of on that cusp between mass production and something special. They are very popular to mod so the unmolested ones will hold their value better in the long haul as fewer and fewer examples remain stock, but time will tell on how badly they depreciate or hold value.
Just my thoughts.
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