I was in the market for a 911. I had a 944 previously and always liked the 911, plus I wanted to have a backseat to take the kids for a joyride. The color, money, and condition were right for the Boxster, but the 911 I test drove was in sad shape.
I picked up my 2000 Boxster in Aug '16 with 135,000 miles. Changed out the spark plugs and one tube, oil change, transmission fluid, getting ready to do the rear control arms, but otherwise is in very good shape. The kids help with the maintenance and are rewarded with rides which makes all their friends jealous.
Because we move around a lot for work, I convinced my wife to let me get a Cayenne to tow the Boxster when we move. Two weeks ago I picked up a 2008 Cayenne S.
