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I also thought about moving to a 911 when we replaced our Arena Red Boxster. Ultimately, I couldn't justify the price difference. The 986 Boxsters are pretty well fully depreciated and good ones can be had for not a lot of money. The 911 still commands a pretty hefty premium, and might be... what... 20% "better" than a Boxster? I know, that's a debate that can go in many directions.
I'd stay away from Audi unless you're really itching to be well-acquainted with a mechanic. BMW and Audi don't age as gracefully as Porsche and Mercedes.
Another consideration for Boxster replacement was a Mercedes SL. At the end of the day that's just a German version of what we already have a lot of (Corvette, GM F-body) so we landed back in Boxster land.
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2003 Porsche 986 Boxster S, Black / Tan
RIP: 1998 Porsche 986, Arena Red / Savanna Beige (wrecked)
1990 Pontiac Trans Am GTA .:. 1990 Corvette ZR-1 (#1930) .:. 1992 Pontiac Firehawk (#010)
1931 Ford Model A Tudor .:. 1967 Pontiac GTO .:. 1986 Pontiac Trans Am basket-case
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