[Perfectlap]

CPO is the way to go in my opinion. I lucked out and found a car with barely 10K miles in showroom condition. In 40K miles I have only had one repair that cost over $300. That's nearly as good as my previous Japanese cars. But the problem is that if something does go wrong the parts are much more expensive and the labor is not cheap either, although Japanese car labor is now well over $100 per hour at some dealers too.

That being said I think you're dealer is being way optimistic with that price tag.
This market is terrible for car sales and particularly sports cars. All these years of unsustainable leverage have bitten the banks and credit markets in the butt big time. Now its hurting car sales. A 15% cut wouldn't surprise me for that Boxster.

I would agressively pursuit this CPO car, but start your offers VERY low. There is absolutely no point in negotiating lightly when you have EVERYTHING in your favor.
They can't afford to let a four year old previous generation car just sit around and they need to get rid of all this old inventory otherwise it will hurt new sales which is where they make their real margins.
I'd take at least $6K off my initial offer just to test the waters. They will surely say no and come back with $39K or something. If they go lower than $37K you know they are feeling pain. Which means you have them right where you want them. Offer $500 more each time they say no. Even if this goes on for weeks its worth it. That car aint going anywhere. I think most people in a position to buy a luxury car now are buying new not used. Whatever happens demmand they stick to the CPO...no compromise.