I currently own both - '00 986 S and '03 996 C4S. My Box does handle better in the twisties but it's also got a race suspension. The 996 is more practical with more space and still handled well enough that I could keep up with a group of sport bikes through the twisties yesterday at triple digit speeds.  Unless you're going to drive at ten tenths, the 911 will handle just as well as the Box at reasonable speeds. My 911 is more than fast enough and quick handling to scare the crap out of you!
I don't know.... I love my Boxster, but the 911 just has something about it that makes it more "special". My lady and my kids definitely prefer the 911 and it's the only Porsche I have that ALL of the neighborhood kids have asked for rides in. I'd personally pick the 911. Early 996 C2's are just dirt cheap right now and the power differential you'll get over a 2.7L or 3.2L Boxster is certainly a big plus.
Kirk
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2000 Boxster S - Gemballa body kit, GT3 front bumper, JRZ coilovers, lower stress bars
2003 911 Carrera 4S - TechArt body kit, TechArt coilovers, HRE wheels
1986 911 Carrera Targa - 3.2L, Euro pistons, 964 cams, steel slant nose widebody
1975 911S Targa - undergoing a full restoration and engine rebuild
Also In The Garage - '66 912, '69 912, '72 914 Chalon wide body, '73 914
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