Re the discussion, I do wonder if it's to do with weight, with lighter riders having more of an issue. I come to this conclusion from seeing a similar thing with Master SHK's micro scooter, when he was first scooting on it any small surface inconsistency in his path and the wheels would stick and he'd go head over handlebars, but now he's older/heavier this doesn't happen anymore. I don't think his riding style has changed, so imagine it's to do with weight/momentum on the wheels.
I certainly have more issues than Mr SHK when it comes to (eg) kerbs which aren't dropped flush, partly as I don't bunny hop (ever) but I suspect partly because I'm light enough to be derailed where he's heavier...?