It's definitely a tough decision. First world problems, though! ;-)
I was where you were at before buying the 4C. That car won my heart, and I couldn't do the Cayman after seeing the Alfa. But it's not really a suitable daily - neither is any Lotus although the Evora comes close (but is still a Toyota made of Tupperware). If we could get it here, the new Alpine 110 might be a suitable comparison. But we can't, so it's moot.
Will the Cayman give you enough storage? The Z is positively cavernous by 2-seater sports car standards. And not particularly low or small to get in and out of. I test drove a GT4 the other day (again, couldn't see myself parting with my 4C for it, nice as it was). it definitely is going to be more difficult to live with than the 370Z. Also, consider the visibility out of the mid-engine car if you are dailying it. Backing out of parking spaces and merging/changing lanes "by the force" gets old fast, if that sort of thing figures into your commute.
The Porsche is a performance car which you can track, and also comfortably cruise anywhere in. The more performance-oriented you spec it, the less daily/GT-worthy it becomes. If you want something with amazing performance and is still a comfortable daily, then you move into 911 territory (or a McLaren, or a Merc AMG GTR, or even go with a less expensive performance saloon car in an Alfa Giulia Quadrifoglio, or a BMW //M-something or Audi S5..., any of which will match or better the Cayman you are looking at in terms of performance and handling). I know - I'm not making your decision any easier! :-P
When the decision comes down to dollars / performance / and utility there are always compromises to be made. I always liked the saying "Good, cheap, fast - pick 2" with regard to having work done. You can have a good job cheap, but it won't be fast, or a fast job cheap but it won't be good. Or a good job fast, but it won't be cheap. I think you'll find a comparable result in your deliberations!
In the end, if your heart is set on the Porsche, and you can at least live with its cost to buy and maintain and the compromises that it may demand of you, then go for it. That is the kind of decision that you need to make with your heart, and not your head.
There's no wrong answer, except to wait because you're afraid of making the wrong decision!
Interesting thread. Looking forward to more input.
Oh, and be wary of Rennlist - it's not nearly as friendly, helpful, and accommodating as this board. ;-)
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