I bought my 2000 S a few years ago with 103k miles, now I am up to 117K. I did the IMS bearing before I picked it up. The previous owner had recently done the clutch but elected not to do the bearing. If you combine the bearing replacement with a clutch job, then the cost for the bearing drops considerably, since most of the labor is an overlap with the clutch job (figure maybe $3000 total?) At your mileage you could be getting close to new clutch time.
I agree with the $2000 per year. Mine is running well, but I had a scare recently where I thought I was going to have to do an expensive service to replace variocam chain pads. Luckily it turned out to be a false alarm.
This past weekend I took the car out to Sebring for a combine DE with the Citrus and Suncoast PCA regions and had a blast.
Lap of Sebring in my 2000 Boxster S
I have been loving the car. They are great cars.
Steve