As someone who has literally lived in AirBnB apartments for a bit over a year now, these situations tend to work out well for me. Most of my stays have been with people who manage a number of apartments on AirBnB to make their living, whether via owning the building, or, more often, by subletting a bunch if apartments (legally or illegally).

Making no comment on the effect of such operations on housing costs or other such matters, AirBnB, like Uber, has succeeded by making a uniquely good user experience, even as they flout regulations and the law in general.