Have you actually tried carrying a motorized longboard? I did. They ARE bulky. That's what actually stopping me from riding a board to do my groceries. And I wouldn't even consider riding it to the office.
But, who knows, maybe these guys will be able to make a board that is not ridiculously bulky. [Make a lighter 10 lbs version, with 5 miles range, and I'm yours. Even for 1k.]
I've seen a good number of people bringing longboards into coffee shops and places like that. I'd imagine it would be harder to bring it into a fancier establishment, though.
How does the skateboard avoid this? Where do you park it when you go to a restaurant or something?