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Farhad--
It sounds like the Smart Car makes a lot of sense for a certain demographic-- guys like you (or like a lot of friends of mine 10 years ago) that live in SF or a similar city that think Candlestick Point is where they'll sail off the edge of the earth. Clearly they arent trying to sell to me and my 2.5 kids and their soccer balls-- it would be as ridiculous for me to buy a Smart car as it would be for you to buy an SUV or minivan.
The Smart might make sense as one of two cars in a family where someone has a short commute, too, though, I think, not if the commute involved a freeway. Also a small demo.
So, questions--
-What would your mileage be like in real-life situation?(coasting down hills? In a car with mediocre brakes?). Nobody drives with a light foot all the time.
-You say that the freeway was intimidating. Fine, if you live in SF, you may not need to get on the freeway much. What about a major Expressway- type street? Harder to avoid.
- I think that this is the most important question-- could this be your only car?