I have a friend with a Smart. He had one of the first ones delivered, and we were in a parking lot, and were swarmed by young women. I could see the appeal of the car!
However, his ownership has not been positive. The car has been plagued with problems, and after the warranty expired, his wallet took a serious beating thanks to Mercedes-style parts and service prices.
Sure, an Echo HB has less cache, but it's a super-reliable car, can carry four people, has "normal" sized tires that don't cost a bundle, gets $29 oil changes at the dealer, and has similar fuel economy to the Smart. Therefore, as I see it Smart = Stupid.