I have had two 986 Boxster S and 2001 and a 2000, handling was great and nice driving position and om a recent PH run one murdered some of the big boys in the twistys
But If you go with Porsche original parts and specialist servicing (at least up here) can be expensive to maintain
As mentioned read up on IMS issues but this is relatively uncommon - but does give you nightmares every time you hear a strange noise from engine.
Other things that go wrong are front springs break frequently, the rear mail oil seal often leaks and this is a pain in arse to sort time wise and can knacker the clutch.
If door membranes go water will get in and with the door control module and ECU being under passenger seat this can be expensive
Front control arms can creak and groan but not too expensive to replace
Gear boxes often need a refurb at about 60k and various bushes can go around this mileage
Brake discs rust very easily and are a common mot failure
A strange one is the keys lose their remote function and they are over £100 plus the coding time to sort - £300 it cost me for two keys
They are now also getting to an age where the early ones are requiring all the break pipes replaced due to rust
As for prices they are still going down and this will keep happening for foreseeable future in fact good 944/968 are getting better money than the very early Boxsters