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When I was in your boat, with a second child in 1995, I owned a '90 Miata and an '84 Alfa Spider. I solved the issue by selling the Miata and buying a '94 Mustang GT convertible. Problem solved!
I moved from a 2000S to a 2003 996 cab almost three years ago. I don't track my car or drive it that hard our roads are pretty straight and flat. I like the 996 just fine and am glad I bought it. I can't really say its more fun than the Box. More power, yes but not overwhelmingly so. Everything else about it feels very similar.
Don't get me wrong, I was looking at 996's every night and I feel I got a great one. I do think decent 996's are at a pretty good spot on the depreciation curve so it was worth trying it out.
Thing is during my nightly car searches, I seem to look at Boxster's and Caymans, neither of which solve your problem but that's where I'm at!
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