I swore I'd never buy new again (I live in Chicago and work from home, so rarely NEED to drive), but after months of looking for a used Cayman or 911 that fit my needs, I bought new. If you can find gently used and Porsche Certified, I'd recommend that. Of course if you want the features of the new model year, you only have one choice
My next car will definitely be used, but considering I want an air cooled 911, I don't have much choice.