I would have sold in 2008 if not for the credit markets tanking. I was at 50K miles at that point. But when values plummeted I reconsidered, although the depreciation was not as bad as 996 Carreras since Boxsters weren't priced that high to begin with (more height to drop from). I was also hesitant to make a big purchase during the slow financial recovery. And its seems Porsche were hesistant to retire the 987 too soon as well. By the time the markets recovered the prices the Boxster was fetching was not worth selling. The values recovered somewhat but at this stage selling now would not put me into a hugely better car. It would just put me into a slightly better car with a big outlay of cash to bridge the gap. Hmm... diminishing returns.

p.s.
My major maintenance list was so long and so much time went into the car that i would be doing someone a big favor selling now.

This fits my 01S. I bought it when it was 4 yrs old, a CPO w/ 15K mi on it. In the 2.5 yrs I owned it, the following was replaced:

rt rear wheel bearing
lft front bushing
RMS
pwr steering pump
driver's window regulator

And that's what I can remember. I was getting to know my service advisor quite well. The first 2 items listed weren't covered by CPO either. Owned the car 1/2 yr after CPO expired and was scared to death of the next item that would break because it would be on my dime. But the issues I had were typical 986 issues, which you read about all the time on this forum. I was lucky and didn't have the coolant tank failure or cables snapping or rear windows cracking, which are also typical to the 986. Traded it in w/ 48K mi.

Bought the 08 S LE (that's what I traded my 01S for) new and have owned it almost 6 yrs. It had the 2 issues I listed in the earlier post. Not bad for 6 yrs and 35K mi. One of the best cars in terms of quality and reliability I've ever owned.

Bought an 07 Cayman S with 17K mi that had 1.5 yrs left on the CPO. I put 18K mi on it and never had to take it to the dealer in the almost 2 yrs I owned it. I did 2 DEs with it.

Bought my 08 Cayman S Sport with 7400 mi and it had 9 mo left on CPO. In the 10 mo I've owned it, I've put 8K mi on with 0 problems. I've done 3 DEs this yr with it.

Based on my experience, these three 987s have been way better cars than the one 986 I owned. To reiterate from the earlier post - a total of 51K mi and 2 problems in 9 yrs of ownership vs 35K mi, 5 issues, 2.5 yrs of ownership. The 986 wasn't a lemon because the majority of forum members have had the same issues. The 987s are not perfect - the one main issue is the water pump. But I can live with that vs the constant crap that keeps breaking on a 986.

Your mileage may vary.

You have gotten your car sorted and know the history. Thats a big plus.

But if your not happy with it and want the S, I would get a early 05 Boxster S with the sport chrono. No TPMS sensor to worry about, different interior layout and ALSO the sport button which tightens the suspension and increases the throttle response. When the tech told me about the throttle response, I was confused because that's what my foot does right? Well after I tried t out it was kind of like this.....:D

Men in Black - Tunnel Scene - YouTube

Its two cars in one.

Test drive an 'S' and trade up it if makes you happy. Don't drive a sports car if it doesn't make you happy.

Next time GET A PPI...unless you have learned to look for all those normal wear and tear items.