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Ooof, so many things to address. The fact that you even ask question 1 makes me question whether or not you're ready to be owning a Porsche.
Which leads directly into question 2- unless you are a DIY kind of guy, you're going to be paying a lot. Parts are hard to come by and are downright murder sometimes.
As for question 3, you say "aggressive driver" coming from a mustang. Does that mean you like to drop the clutch a lot and do burnouts? If so, the Boxster is not the car for you. It is as 180 from an American muscle car as you can get. These badboys were made for corners, and you'll be disappointed if straight speed is what you want.
As for what year, I would suggest getting something with a dual row to avoid IMS issues.
Happy huntin'!
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