That did seem like a lot.
I think local market really comes into play here unless your willing to travel. Maybe i am wrong but the same car in CA will likely cost less than the same car in MA. Prices here are stupid dumb. I traveled when I got my Box to PA from MA. I think I saved a bit.
Pro's cons List
Perfomance 911
Back Seat 911
Well Sorted/never beat on: Box
Boxster Mods done (won't get back in trade in and will most likely hurt) Box
Bought and paid for Box
DIY Wash
Resale God knows.
Cool factor: Box #113 of the first batch of Boxster S's and made in Stuggart. Hey if 911 guys can say only one made with purple seats, I think this has some value.
Underdog coolness Box

I see them at the track, they do pretty well.
Visually Appealing Box (IMO, I know some go "oh god,, what has he done".
Mileage 53k vs 95k Box
Name Factor 911 (though I believe the 986 will have it's day)
Kids in School : Box
Explaining to Wife more money on car purchases: Box
I made up a few categories to help the Box, some are in jest. Well kind of.
Anyhow, I guess I will test drive and go from there. If I absolutely love it, I may have a problem.
Thanks everyone, these 1st world problems aren't so bad to have.