2009 Boxster or an 08?

[Perfectlap]

Find a low mileage certified pre-owned 3.4 S!
Sounds like you are responsibly minding your finances, that said you have a great deal of bargaining power in the current soft economy. New Porsche sales are down sharply in 2008.
That puts downward pressure on the price tags of certified pre-owned Porsches, meaning they are the best bargain going (as far as depreciating assetts go).
The dealerships have to move these cars before inventories of old cars start to mushroom, hurting new Porsche sales. Furthermore 05's still LOOK EXACTLY THE SAME as 08's. Those 08's will take a big big hit on depreciation in this current economy that is only going to get worse. The dollar has taken a brief pause in its drop but the long term outlook is not good. Fewer and fewer Porsche buyers means less demmand and lower values.

The conventional wisdom is to do the opposite of what your dealer wants you to do. I'm guessing they want you in a 2009 first, 2008 second, a 2007 third and a CPO 05-06 third. To each his own but I've never heard a good argument against buying a CPO. These cars are gaining Japanese level reliability.