And both are primarily successful because they have executed at a very high level on a consistent basis.
Secondly, Uber got big using exclusively licensed town cars. And vacation rentals have been around for centuries.
That's very meta!
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.