I happen to think that Boxster's are very capable cars. I am not a huge fan of verts, so I think the Cayman is a better looking car, but still, the Boxter S is a very nice ride. I do not think of it as a "chick car" nearly as much as a Mini or VW Bug. How it performs on race track is what really matters with a Porsche and I have seen some very fast Boxsters out on many a road course.
Someone mentioned it earlier, but the rear main seal for the engine is the "Achilles heal" on these cars. It is my understanding however that a special tool was developed to change it in a fraction of what it used to take. I could be wrong however.
I do think that Porsche lost their way a bit with the 911. It started to get pretty heavy and laden with luxury garbage many people did not care about. Of course the GT2 and GT3 models have held to the 911 roots.
Growing up, I always wanted a 1977 930 Turbo. I always thought that is/was the best looking Porsche of all time...4 speed manual and all.
And somebody mentioned the 917 earlier. Do yourself a favor and visit Road America the third weekend of any July for the Brian Redmond challenge. There are usually a few 917's that show up. The Porsche 917k and 917/30 models are some of the most incredible motor vehicles ever made. A 917/30 in full Can Am dress sporting race boost pushes 1300-1400 HP and their acceleration down a straightaway is breathtaking. The engine oil on these cars is actually cooled through the tubular birdcage and they had technology that was decades ahead of its time.
If the right Boxster came along and I was getting sick of a few machines, I would make the trade in a heartbeat.