I posted the following in another thread, and I think it succintly encapsulates the OP's question of when a 911 is no longer worth it:
Quote:
I guess I'm not interested paying "new car" prices for a 25 year old DIY hobby car.
When I buy a DIY hobby car, I want to pay DIY hobby car prices.
Yea, I guess that sums it up.
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The dissonance I was having is that I was approaching this as a hobby car,
where it's really crossed into collector car territory (or a mixture of both, in reality).