A 1999 Boxster with 100,000 miles has already dropped to ~$8,500 on KBB and every model year thereafter is on the same downward slope. There is almost no intrinsic Porsche brand value that is retained in a 986 Boxster - its a used car and not much more. Of course, well cared and well optioned cars will always be worth slightly more.
If you love the car like I do, then I could care less about re-sale value becauase its all about DRIVING value!