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For me, a car has to have heart. Its that kind of feeling you only get with your special lady. Indescribable. I think, for you, that might be the sort of quandary you are dealing with. The cayman S seems to hit all of the obvious points but is missing that one crucial aspect. That heart. At least thats what it seems like you are saying.
I don't think that heart is necessarily all that attainable anymore with newer cars. Maybe that's why the biggest car romances seem to be with the very old 911s? Ive never driven a cayman, so i cant comment, but it seems to me like that might be the best option for what you are after. It will be a compromise though.
Somewhere, there is a video of Chris Harris saying that the e46 m3 is the last best sports car (or something along those lines). I think he would have said that the z4m was if he had a reminder, but that's a different story.
The point of all of this text is this, I dont think you are going to find a car that marks all of the boxes, so at the end of the day its about the compromises you are willing to make. If i was in your situation i would probably be looking at it the same way. I say buy the Cayman or wait just a bit longer to find something that might be a little closer to what the all around package looks like to you.
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