bullwinkle
That's a lot of questions! All of the answers (opinions) can be found on this forum by searching many of the keywords that are in your post. I will give you my opinion, which you should not take as fact.
You are unlikely to experience such little maintenance on a Boxster as you did on your RSX. A set of high quality rear tires will last you at least 10,000, but probably no more than 20,000 miles. Be ready. It's not fun once the tires are past their wear indicators! You could easily have the same type of repair history on a 986 as you did on your RSX, or you could have a repair history like that on a semi-annual basis. There is no guide for you on this one. Just be prepared.
At 7 years of age, you will find a warranty difficult.
Many warranty companies have a cut off of 5 years of age at the time of purchase. Porsche will not CPO a 2002 today. They may, however, sell you an aftermarket warranty at your dealership. There are many warranty stories on this forum (search 'warranty.') Some are awesome & confidence inspiring. Many are not. Porsche's OEM warranty on cars with less than the maximum age/mileage seems to be great, however, and they tend to replace whatever breaks without question. You would be looking at a 2005 (987) car at the oldest, though, and they are definitely more expensive (initially) than a 2002. Maybe that's out of your $$$ range?
IMO an S2000 & a Box are only similar by the facts that they are 2 seat convertibles, and (unmodified) they should produce "similar" lap times on a track. One has a classic look, the other doesn't. One has an insanely buzzy, cacophonous motor, the other was once described by Car & Driver magazine as "sounding like God's own organ music," which it does! You will have to drive them both (drive different ones too - try at least 2 or 3 of each - why not?) Many S2000 have been slightly tuned & tweaked so one may be stock and the other may have belonged to a boy racer who doesn't mind bleeding eardrums or porridge for kidneys. To put it simply, I drove both, have had plenty of service woes, and still agree that I didn't want an S2000. I would not rule out entertaining an eventual replacement, but it just seems like that car hasn't shown up on my radar yet. The 370Z is as close as anything has come (but a CPO Cayman S is more appealing.)
Do as much research as you can on this forum & buy a few Porsche magazines. There are numerous articles on Boxsters. Most of the posters will respond to your questions right away if it hasn't already been answered often. Before you make the purchase, spend a good month on the forum if you can. This will help you to know what to look for and the proper procedure to purchasing a pre-owned Boxster.
