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I'm only gonna answer couple of points:
#2 - The M2 is awesome but nowhere near as practical as M3. Rent a small 2 door car for a week when you know you'll have deal with passengers to get that experience.
#3 - I'd hope you can get more than $22k for 5 year old M3.
#4 - based on what you said about the M3 I don't think automatic is for you
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