I like to buy distressed things and fix them up (then make them distressed again). I am not a long-time Boxster guy, but got in pretty deep about a year ago. That said, I would still easily pick #2.
Basics:
#1 Higher miles with 2x the wear and worse cosmetics. Was not owned by an anal Porsche-phile. Low cost to get in, high cost to get right. If you DIY, you can buy couple thousand in parts and really get to know your car better. The $6K that you are saving over #2 has been 'driven off' of #1 and it is still a lesser optioned base model. Unknown maintenance history (Original water pump and motor oil?)
#2 Cared for and documented, manuals have not been lost. Practically 1/2 the miles and only 1 model year older. Well Factory optioned and S.
I have not studied the 05-06 well enough to know the particular flaws of each year, but I'd guess that #1 is a lot closer to exhibiting them.
Good luck and post pics when you can.
