Having owned a 2008 Smart Passion, I will say it is a surprisingly well engineered vehicle. You will find many consumers complaining about the transmission. Most magazine editors, consumers and tire kickers don't know how to drive the Smart. The car technically has a manual transmission. Have you ever left your foot on the accelerator when shifting into the next gear? If so.....you will notice something bad happen. The car will not go smoothly into the next gear. Same with the Smart....Let off when you want the vehicle to shift, and reapply your foot to the accelerator. For optimum performance and making an extremely happy Smart, use manual mode and shift up let off the accelerator and reapply your foot to the accelerator. The Smart is a blast to drive, and ideal for urban dwellers.
Regarding the 09 Honda Fit. It's a no brainer....Sporty, spacious, far superior to it's predecessor. Toyota also has the Yaris in both a 3 and for 09 is offering a 5 door. The B class segment is increasing in popularity by leaps and bounds. Whatever B class vehicle you decide to choose, it will hold a great deal of resale value throughout many years of ownership.
http://www.youtube.com/watch?v=CurSap0Dxlc