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Kirk is 100% right on the whole box vs 911 thing.
My brother in law has a 1999 996. It's beautiful. Sport Technic wheels, full aero kit, litronics.... for a "standard" 911, it's gorgeous. I've borrowed it a couple of times, so I've had a fair amount of seat time in it.
It's faster than my boxster, and it turns more heads. It looks more prestigious - BUT if you were to tell me that I was about to go out for a fun drive on a mountain road or a race track - I'd rather have my boxster.
the boxster handles better and is more fun to drive. Period. No comparison.
Maybe a newer more modern 911, would be such an improvement over his "older" one that I would not feel the same way...but if you're considering an "older" 996 vs a 986 - I honestly think the 986 is the more fun car.
if you HAVE to have back seats, or do NOT want a convertible, I think it would be an awesome car. It's not like I didn't like the car, but if you are looking for pure driving "fun" I think the boxster is better.
I second Kirk's idea to go test drive some and see what you think.
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Cars:
2007 MDX - Wife's mommy mobile
2006 RL - My daily driver
2000 Boxster - Ocean Blue Base 5spd on Black Full leather. 18" wheels and M030.
Boxster mods I've added: Rear speaker kit, Painted Calipers, Painted Bumperettes, Painted Center Console, 987 Shifter Assembly, 3 Spoke Steering Wheel, Clear side markers, 03+ rear lights, de-snorkeled.
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