Storminmatt - you sound like an Insight hater too. Anything that doesn't fit YOUR idea of what a practical car should be just isn't a good car.
The Smart is practical for ME and most likely would be practical for people in similar situations as me. 2 people who commute together. Let me guess, you've got 4drs on you car but 90% of the time all the other seats besides the driver seat go unoccupied. My ONE passenger seat in the Smarts go unoccupied maybe 2% of the total mileage that have been put on the car. This makes you a very wasteful person by letting those other seats go unoccupied.
Now that you read that - it's obvious that I've never ridden with you and I'm only speculating and just getting you roweled up . Just like you are doing with the Smart right now, but until you get some credible wheel time on a Smart - please don't hate. I have seen many haters change their mind once they actually study up and learn about it - it is almost similar to being prejudice though it is an inanimate object.
All that said - you are correct about the premium. Out of 52 tanks of gas on my car with 16,500 miles I've gotten 3 that were below 40mpg with the last 3 being 44mpg. BUT - do I really car that my care is comparable to a car that get 41mpg, NO! How about my time saved when I didn't have to search for a parking spot, take my passenger and my hourly rate we make and then divide that into time saved because we're in such an "unpractical" little car and it start to tip the scales a bit. This car has honest to goodness saved me HOURS in the last 5 months of ownership on searching for parking spots. Once again - my scenario and others may differ.
It cracks me up you're worried that you have to drive a car that LOOKS like a car. I'm guessing you live in one of those neighborhoods that all the houses look just alike too. Don't follow the herd - live a little for once stop trying be like everyone else and be an individual. The very reason you don't seem to like it is the very reason I love it.