Fiat 500

Price: $16,250

For this round of WYCB I chose a car that took the hearts and flirted with the minds of a lot of people in the US. Finally the return of the quirky Italian company even if it was grasping the hand of his big brother, Chrysler. Popularity is in a continuous rise as is its lineup, but this time the prospect buyer wants the original. Fiats house special. He isn't too concerned with reliability or practicality but emphasises on fun and "Joie De Vivre!". As it is with every case, there are other options available as I will demonstrate bellow.

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1. 2004 Mini Cooper: $4,950

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This was also the return of a retro-icon that captured the hearts of people who wanted basic transportation. Now, its a FWD BMW. The Mini is a drivers car, even if it sends the power to the "wrong" wheels. The feel of the steering, the gearshift and the lightness makes it a hoot to commute in, even more than the plucky 500. At this price, repairs can come and it won't make you feel so hit due to its low entry price. More power, better perceived quality and similar quirkiness makes this option one hard to beat.

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2. 2008 Mazda Mazdaspeed 3: $11,950

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This will make your commute hair raising as your wrists try to tackle the steering wheel as a desperate 12 year old tackles his Xbox controller when being ambushed in Call of Duty. Its a seriously aggressive car, sort of how a FWD WRX would be. The added bonus is a Mazda shifter, steering feel and overall character that everyone likes to think is a carry over from the Miata. Although not a 2 door, this car is fun enough to compensate from the somewhat sedate appearance.

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3. 2011 Volkswagen Golf GTI: $16,991

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I may be showing my fanboyism towards VW, but the GTI is a great car even if you hate Germany so much you don't even touch sausages at BBQ's. The torque from the engine, the crispness of the transmission and the plaid seats insure you will have a great time, even more than the 500. The liveability will be much higher whilst still having a bright color in a 2 door body-style. At less than 50,000 miles these can still be bought CPO with a warranty which is what I would go for 100%.