I don't think there is a right answer. I was between moving up and going SC on my Z. I did the latter of the two. Apart from sentimental value, there's some charm in the sense that the car was never necessarily engineered to go that fast, as opposed to a 992 which comes more ready/refined.
Something different in my scenario, though, is I've been nowhere close to entertaining a 911 (even a 997 gen). I don't know how long your window is to be able to shop such a car, compared to how viable it is to find yourself in another Z if you changed your mind.
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