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I wanted either a 1970's targa or a first gen amber/cable throttle 996 coupe- 997 didn't interest me. I couldn't afford the targa, and found a cab instead of the 996 coupe, but still very happy with the car.
I certainly did not anticipate quite how much work was going to be involved that's for sure, but then I am trying to become, in effect, the first owner as it were (this has just occurred to me), so everything is being returned to as close to factory fresh as I can.
I'd classify this with your Vespa Niall- it's past any economic point of return, unless things change dramatically over the next ten years in terms of 996 values anyway.
I'd sell the Volvo now, if I got the right offer, I don't think I'd sell the 996.
Dammit
Out of interest what would just spending £31k on a 911 have bought you? Apart from a mint 996 or 997 Pistonheads has one decent-looking air cooled cabriolet.
If there is a lesson here it's that you're a perfectionist and can never be satisfied with a car that doesn't look and work like it was brand new, and either stop buying used cars, or always buy the very best one you can find. That mostly worked for me on the Porsche. I hope it works for me on the Aston. I guess we'll find out :-)