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Interesting thread. Being an ex Boxster owner having owned a 2001 Boxster base for three years, sold it last year please allow me to express my opinion.
Above questions are so relevant. What are you going to use it for? Tracking, daily driver year round? I drove my Boxster year round for 3 years including driving in -20F. Can it be done? Yes but it is likely harder on the engine due to driving in extreme cold. Net result was green crud in the oil filter and was possibly due to chain guide rails breaking up.
Would I do it again? Possibly but not being my own mechanic meant that I am at the mercy of a P mechanic. My next move is an older Miata which I had before the Boxster as it is cheaper to fix.
Make sure there is warranty left on the one you choose as you seem apprehensive.
Make sure you get a PPI done before you commit. A lot depends on your financial situation which is none of my business. Once off warranty all bets are off. The amount of $$$ you are putting out is substantial so I hoping that once off warranty you will be comfortable if something goes wrong.
As for myself I likely will come back to a Porsche(Cayman?) because once you have owned one it is in your blood. And you will enjoy the ride.
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