As a tech who's worked at Nissan and now works at Porsche, I have to say they are COMPLETELY different cars.
Z is a front engine, tail happy vehicle while the Cayman is a mid-engine car that just seems to stick to the roads so well on every corner. Which scenario is more fun is all up to you.
The brakes on any Porsche are far better than the Z (even with the akebono).
Both cars have different yet distinct exhaust notes.
IMO the Z looks better than the Cayman; parts are FAR less cheaper for the Z.
Maintenance isn't too bad on the Porsche, especially if you're a DIY'er
And if you are a DIY'er, it is quite a bit more time consuming to work on the Cayman (vs the Z) as there are several covers/panels that you will need to take off to access the top portion of the engine and as well as having a lot less room to work with.
The Cayman S has a much better engine than the base Cayman so make sure you go with the S if you do get a Cayman.
Like most people said, the Porsche does seem to be much more comfortable as a daily driver while still being very aggressive when you want it to be.
If I had to choose, I'd pick the Z again since it's much cheaper to modify, looks better, and just seems less forgiving with vdc off; which makes it more fun in my opinion.
Although, one really cool thing about the Cayman that I could never get over was the fact that the engine is literally right behind you. You can take off the covers right behind the seats and look at that engine running right next to you. I just think that's so awesome.
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