First gen Caymans and price
 

With all the bad rap issues until the fix in 2009, I am surprised at the high asking prices of the older ones!
I see 2006, 7, and 8 as high as the 2009 and forward.

If I was buying one and the difference is nil price wise between 2009 and back, it is a no-brainer to move in on the 2009 and newer.
At least that is my logic, what am I missing?
Why would I pay the same price (about) for the first generations as the 2009 and fwd?

The early cars don't have direct injection, and are therefore a bit less maintenance-intensive (although slightly down on power--20HP, I think?). I had a 2007 Cayman S and it was a pretty sweet car.

For starters, it does NOT have the same IMS issues as the M96 cars. It's a different design on all but the earliest ones and a different far more "intrusive" repair. Beware the narrative those selling a fix have put out there, it's not really true and more intended to make money from fear.

I own a 987.1 S with 175k mi that just had the engine rebuilt. It broke a valve spring and dropped a valve. The bottom end looked like new. Put in a new factory IMS bearing and did NOT do the fix. I consider it a non-issue.

To the rest of your question, are you comparing apples to apples? I tend to see 987.2 Non-S cars around the same price as 987.1 S cars. I would be interested in some links of what you consider comps at similar prices because I just haven't seen equal condition S models across the generation that tightly priced to each other.

I think Matt is right. My good friend has a nice 08 Cayman and one of the main ims fix it companies is always sending him the cost for the fix. But then on earlier info in their literature , they have said there was very little ims problems in the Cayman. Big money for the fear.

Also, Southern California seems to have great prices on early Cayman’s.