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I'd always recommend to someone new to Porsche to try both the 911 and the Cayman/Boxster. They're both all-time greats IMO, but some people will prefer one to the other. And some (like me) will want both.
That said, I would be stuck with the mid-engine models at that price point. I personally hate the 996 and would not recommend. But don't take my word for it, give it a try and decide for yourself
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