That regulation is a decade or two behind the technology is unfortunate, but merely a side story.
I also spend a couple nights with family - they don't have any special insurance or taxes for me either. I don't really see any difference, I didn't annoy the neighbours in any case.
That's very meta!
True, but most businesses (outside finance) have other ways to make money besides cajoling, skirting, finagling or ignoring laws (or the latinate "regulations," as you prefer).
"Regulation" (at least in the US) is a broader category, covering both "laws" passed by elected lawmakers and "rules" made by unelected public servants.
Secondly, Uber got big using exclusively licensed town cars. And vacation rentals have been around for centuries.
And both are primarily successful because they have executed at a very high level on a consistent basis.