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For $30k range a 987.2 Cayman or Cayman S gets you into the modern Porsche sports car sweet spot. If the plan is to get a 911 at some point you'll do yourself a favor by getting a highly desired Porsche sports car that you will not lose money on while owning it and driving it, that also will not make you poor.
2009 is a good starting point to do that. And if you can get down with the Boxster then they are cheaper than the equivalent Cayman.
A Cayman of any variety is not a replacement for a 911 of a similar variety (S vs S, GTS vs GTS, GTx vs GTx) But it is still a great car and fun to drive. I say all this having had both a 987.2 Cayman S and a 997.2 Carrera GTS at the same time.
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