Actually, I take it as sort of a compliment. It is up there amongst Mercs, Range Rovers, and BMW's. Most of what they say in this article is pretty accurate about the Smart too, and not too negative :)
The Ten Preppiest Cars
Yeah, This Isn't Very Smart - smart fortwo - Jalopnik
So by their logic if you purchase a car which doesn't fit your camping equipment or whatever once a year and you have to take a trailer or rent an RV or something, you are not very smart? I actually think that guy's makeshift trailer is genius.