Ooh, that's no good :/ the controller loses connection when you're riding - is that a fairly common occurrence?

It's only partially the case. I've taken pretty bad spills before because of unfinished road tar that pretty much "ground me to a halt", like quicksand, and also from curbs that I thought I could brace, but instead sent me forward head over heels. Skateboard accidents can be a lot less forgiving than bike ones if they are the kind where your board stops and you keep going.. Though they also can be a lot more forgiving since you are closer to the ground. It's a mix. I don't wear a helmet -- helmets makes me more clumsy. But at the same time, I don't really go in the street much, mostly a sidewalk skater.

Still a problem though because you have to be a lot more vigilant on board versus a bike. A bike can somewhat "hop" an obstacle that the wheels might not be able to roll over. The board on the other hand will most likely send you forward as it abruptly stops.

Yeah, bigger, softer wheels + higher speeds + 2000 watt motors doesn't compare to a regular skateboard with small, hard wheels.

That said, it also doesn't compare to bicycles with ~26" air-filled tires. You definitely have to pay close attention to the road surface.

I don't really think there's a way to make a skateboard safe at speed. Ultimately if the skateboard stops suddenly, you continue to travel at the speed it was going, and unlike a bicycle, nothing is going to absorb damage except your body.

Yes, it certainly appeals to me. I like the idea of doing things dangerous enough that one must actually focus and pay attention.

I went right back to motorcycle-riding after the bolts in my thumb healed up. :-)