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That's not a bad looking car and doesn't look abused to me. Cosmetically, outside of the bumper, I see normal wear. Heck, the shifter on my 2000S looks worse than this one. I doesn't mean the car hasn't been cared for, I know mine has.
The car has a maintenace schedule that lists items that should be inspected and replace at 60K miles. None of the items are terrible, nor hard to do yourself if you are so inclined. I would ask for records of maintenance performed during the sellers ownership.
Rotors, pads etc. should be accounted for they will result in a $300-$$600 bill to renew.
Source of oil leak is a big one from a money differential standpoint.
If the oil leak is the RMS, you will be looking at ~$2k worth of work as it is the most cost effective time to replace clutch and IMS bearing. If flywheel needs to be replaced, add ~$700.
The bumper is not a big deal...I've had front bumpers repaired (stone chips) and repainted for under $500.
Go look it over and drive it. You have nothing to lose, except you will really want a Boxster once you've driven one!
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