and the 49k miles doesn't scare me, nor does the 5 owners. Surprise. Roadsters are owned by people whose circumstances change. I bought 2 Boxsters. First from a lady who was replacing it with a Hummer because she didn't drive it any more and now had 3 kids. Second from a salesperson who needed more room and a more all weather car and who couldn't deal with a set of snow tires for it. This last car was bought from a motivated seller in January when the car was covered with snow and salt! But because it was, I got a bargain. Both cars were 2 owners-before-me cars. Both original owners traded them in during the first year. Both cars have had very very few problems.
My advice is go to craigslist.com for Chicago and watch the adds (none there now in the medium mileage range) . Remember the asking price is at least 10% higher than you should be offering. And make friends with the guy who comes recommended as a future mechanic and who will be doing your pre-purchase inspection.
Other thoughts
http://mike.focke.googlepages.com/buyingorsellinga1997-2004boxster