For more than a year, I commuted to and from work (3 miles each way) on a lightweight electric scooter I bought on Craigslist for $100. It's been a while, but I used to skateboard, surf and snowboard, but having the handlebars of a scooter in an urban environment is huge for me in terms of control and safety. I used to call it the poor-man's Segway.
I think that taking this [1] rather insane idea for a "longboard stroller", and replacing the child(!) with one's laptop bag and maybe some kind of fairing would be a pretty sweet solution for those of us not agile enough for regular longboarding.
Lightweight electric kick scooter could be useful to larger audience as a "last mile" solution.