I have both although my Boxster is no longer a road car but it was stock for years. I expected my 996 to be very similar to the Boxster but they are worlds apart. My Boxster is a 97 and my 996 is a 2003 so that may be part of the reason but the 996 feels far more like a real car and the Boxster has always felt like a toy. The difference is in the space, the lack of mid-engine noises and vibrations, the security and low noise levels of an actual roof etc.
I bought my 911 when my wife was pregnant for the same reason you're thinking of getting one and well...I'm not sure it will ever be the family car I wanted it to be. Sure I'll be be able to pile the family in on an occasion or two but it really isn't big enough. I hate to say this but you might want to look into an e90/92 M3....
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1997 Boxster 4.2L Audi V8 Bi-Turbo
2003 911 C2
NASA HPDE Instructor
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