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There's an "///M" 335i convertible in my work parking lot, I gotta snap a pic next time I see it. We've crossed paths and he's seen me in my M3, I think he cringes a bit.
As far as seeing the other side of the coin, I've been on the other side of the coin- seeing everyone with their nice cars and not even having a car of my own. When I finally did get a car at 21, I had no desire to fool others about what it was. I'm not a big fan of the "fake it til you make it" motto. Be proud of what you have and work your ass off to get what you want.
I'd rather be honest instead of trying to make my car into something that it's not. I'm also wasting money that could be saved for that future car.
To each his own I guess, but for me, it just seems like a waste of time and money.
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