The people who say "who cares if you look like a dork" either have a less-important use case for their own public-facing image than others, or exist in a cultural facet that perceives those things as more culturally acceptable. Even some people whose personal appearance is extremely professionally important— lawyers for example— can withstand looking really square because the cultural context they exist in calls for it. If a bouncer at a nightclub looked as square as a lawyer, their job would be a lot harder. A lawyer would get raked over the coals for wearing a club bouncer's poorly-tailored polyester suit. Your appearance influences most people's perception of you, and their appearance influences your perception of them, whether you care to admit it or not.
I mean, I know some people who thought google glass looked cool. I wouldn't wear google glass if it could make me fly.
Speaking of which, now that the Segways are done for, I wonder if Google Glass will overtake them as the cultural icon for dorkiness in the aughts? I heard people explain google glass as being like "a Segway for your face." I wonder if now Segways are going to be "like Google Glass you could ride."
But when a lot of people decide to look like dorks for a while, that effect wears off. Everyone made fun of the e-scooters for the first few months they came out, but they’re just so darn practical, they’re not weird anymore.
I think your right on the other part though. The Segway's target market is people that live and work and play mostly within a 1.5 mile radius. Unfortunately the original Segway was too expensive but more critically, far too big and bulky. The target market which stays within a tiny region are able to do so because it's so dense. But that density means that apartments (and stairwells and elevators) are too small to fit the original Segway. Nor did it fit well in the trunk of a car. Leaving very few buyers outside of Segway tours for tourists.