i currently own an 08 AP2 S2K and a 09 370Z. i think its safe to say that i am not as biased as other members around here on the forum.
I bought the 370Z first when it came out and it sorta wasnt what i wanted, so i decided to sell it and get an S2K. (this whole dilemma was going on last year august?)
Ever since, I have had both in my garage sorta wanting to sell the S2K (i barely drive it around) and keep the Z. Why? honestly the Z spoiled it for me with the low end torque. And it is also easier to live with. (more interior room, larger trunk.)
Do i regret getting the Z? Hell no.
Do i regret getting the S2K? not really.
At the age of 24, the S had everything that the Z was missing ,but in the end, the Z had alot more to offer than the S.
i didnt want to go into much details because you probably read alot of reviews about both cars. Just think about what you would really want. A raw sports car that looks outdated(personal preference) or a newly designed sports car with little amenities that you would appreciate for the next... 3-5 years.