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My final decision came down to a '91 Carrera 4 or my '99 Boxster.
I went with the Boxster. Honestly.. for less money it delivers an equally satisfying driving experience, the same wonderfully operatic flat six whirr, and will be relatively maintenance free in comparison as my daily driver.
I'd love to own an older 911 someday, but I don't feel like I gave anything up by going the Boxster route. Two completely different cars aimed at two different tasks and they both do it remarkable well.
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