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Since you're not going to the track (a waste), you should get the Cayman. I'd recommend the S though, since it'll hold value better, so that even though you pay more upfront you shouldn't come out too far behind in the long run (also you won't suffer from regretting not going with the S in the first place).
If you were going to go to the track, I'd recommend a used BRZ. Anything you bring to the track you have to be prepared to leave there in a crumpled and/or burning lump. You cannot enjoy a trackday if you have the specter of financial ruin looming over you.
a 2006-2008 Cayman S can be found with a manual in good condition for $19k-$25k or a newer 2009-2011 in the $30k's (I don't keep up with the dsg prices, but if I believe they are similar and would be the better commuter option).
The consumables on the Cayman are much higher than a twin and the purchase price of the cheapest S are on par with new twins.
I love autox and trackdays (I'm on pace for over 20 autox events and 15-20 trackdays this year). You gain a whole new love for the car when you can push it to its (and your) limit.
I've had a sweet spot for the Cayman since it came out, and I'm still kicking myself for not picking one up in 2009 when the market was flooded by lease returns when the market nose dived (seriously, I had a chance at one for $25k back then and I couldn't buy the same car for that now).
I'm hoping my 2014 BRZ will last me until 2021, when I'll either get a new BRZ with a bigger motor (if the rumors hold up to be true) or finally grab a Cayman S or 997 911 (depending on how the Porsche market changes between now and then). Hell, I could see myself keeping the old BRZ and relegating it to track duty (maybe throwing on a supercharger, that just really messes with autox classing).
If I were starting over tomorrow, I'd either get a 2015 BRZ and set it up the exact same as my current BRZ (STX autox prepped) or find a 2015 BRZ/FRS and throw a Jackson Racing (or Edelbrock) SC kit with flexfuel and call it a day (that'd be about the same price as the cheapest Cayman S and it would be at least as fast, but I'd avoid the Porsche tax on consumables and maintenance).
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