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I just made this exact choice last month. I had an '87 Carrera Coupe for about 8 years. It was very well sorted-out, and had about 108,000 on it the day it left. I sold it and bought a 2003 Boxster S with 30,000 miles.
The performance of the two cars is quite similar. The 911 felt a bit torquier for sure. But the Boxster has modern controls, so the two cars feel very, very different, and direct comparisons are difficult. The 911 was more "sporting" in just about every way. More steering feel, more feel through the pedals, everything. But the controls were all much heavier than the Boxster, which was tiresome in town. The thing that stands out about the Boxster is its "fluidity." Like the 911, all the controls are well harmonized, but you use them with so much less effort. So it makes the driving experience more an exercise in relaxed precision, rather than 911 style grab-it-and-dominate-it type driving.
The Boxster feels much like most other cars in terms of build quality, but the 911 seemed like driving around in a bank vault by comparison. Even with many fewer years, and many fewer miles on the clock, the Boxster is not as well screwed together. I drove a lot of them too, so it's not just this one being beat up or something. No way it will comfortably last as long as a good air-cooled 911.
On the other hand, the Boxster has auto climate control. In a 3.2 Carrera, switching from heating to cooling is a Rube Glodberg task of comical proportions. The Boxster can haul at least as much cargo, in covered trunks where prying eyes can't see it. But, my wife and I can't take the dog along like we did with the 911.
If I had the garage space, and didn't mind the carrying costs of taxes/insurance/maintenance, I would like to have had both of them. They really are very different.
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