Are you suggesting that, because it takes skill to operate, it's a bad idea?
I commute on my longboard every day between the parking structure on campus and my building, which is about a mile away - takes me 10 minutes of kicking the board around and working up a sweat.
An electric longboard woud fit right into my current commute, except I'd arrive at work without my shirt soaked through.
For this type of commuting, a couple of days practice in a empty parking garage or lot gets you good enough to safely commute, and if the SF hills are intimidating, you can always walk down them.
As for braking, they indicate that the remote does have a brake slider, and by using regenerative braking, they can slow the board down (to some extent). You would still need to know how to brake the board, but the board can stop itself.
This would also be a super fun toy - I already take my longboard out to race down hills, with this I get to ride up before I fly down.
But, a rollerblade version? Can you explain how that doesn't have the same concerns you raised? Rollerblades are even more difficult to brake than skateboards, and you're committed on rollerblades, while on a skateboard you can jump off and carry the board whenever it's inappropriate or too difficult to ride it. There's also zero cost to hopping on a skateboard, while rollerblades involves sitting down and changing your shoes.
I doubt this product will fix all of the transportation woes of the US (which their marketing seems to point to), but it's great for current longboarders and people already interested in unconventional transportation options.