Honestly I think you need to shelf the "head turner" idea and get yourself a real daily driver that is cheap to maintain and reliable, incognito, comfortable, cheap to keep. Something that can go to home depot. I wouldn't take a CL63 to home depot either. You already have a car that is a head turner. If you feel the urge, then just go home and get that. You're going to pay a hefty price for vanity. For 50K you can get a car that hauls shit.. Some sort of wagon or SUV, AND and a luxury car. A comfortable 4 door sedan.
I have a Honda element. That's what I take to home depot. You can get a nice hauler. I'd rather have an 08+ Toyota highlander SUV that has TONS of space, is reliable as hell and has great sale for about 20K, and spend 30K on a Mercedes S class or a BMW 7 or even an M5. 50K is a lot of money for a used car. That or I'd get a Mercedes GL and be done with it. It's still an Mercedes and it is very practical and safe. You can be a "humble baller" instead of an obnoxious one.