[Perfectlap]

I would not buy a new S2000. Its pointless.
You will get the same reliability, performance and looksn from a second hand
S2000. And what a sports car bargain it will be.

I don't believe the Boxster S is superior to the S2000 in any way that is quantifiable. They are in the same league. In terms of styling a well styled Boxster is in my opinion a nicer looking car but that's purely subjective.

If I were you I would either get a warranty for that BoxsterS or look for a second hand S2000. It sounds like you are at the limit on disposable income so a new car really is not a good move, you'll lose money you should be saving/investing on the depreciation of a new car. Also you will get more of your money back buying a second hand S2000 which you can later use to buy CPO in warranty Boxster a few years down the line.