Hey Jeremy,
I actually just spent a month doing what you are setting out to do here. Finally this past Saturday, I bit the bullet and bought a new 2011 Brilliant silver 370Z, black interior with the sports package. From all of the research and haggling I did I was able to get them down to an even $31,000; along with another $4,000 for my trade in (2002 Nissan Maxima GLE fully loaded, heated everything minus the Navi (GPS NOT AVATAR)). At any rate I am absolutely convinced that I made the right decision. I was originally leaning toward an 09 Z but the prices were in the same ballpark, 27K and up. I have an odd question, do you have an American Express card? What set me off on the new car journey was the ZAG site available to AMEX card holders. Its a site that has the bottom line dealer price pretty much nailed down, so all of the major haggling is done for you... check it out here
AMEX AUTO PURCHASING PROGRAM, and if you need any info let me know! Happy Z hunting!