Why would I take that when I already have a running bet with my insurance company where I only pay ≈ 20 USD / month?
The whole point here is that I can afford 20 USD/month indefinitely. However, having my house burn down at any point would be absolutely detrimental to my personal economy, to the point of bankrupting me and likely preventing me from being able to afford a new house in the foreseeable future. I'm well aware that in purely economic terms I'm taking a losing bet. The point is that the consequences should the bet strike home are so large that I can't afford not to take it.
Of course, you could argue that I would be better off saving that money and being "my own insurance". You would be right, except for the fact that the house burning down is just as likely tomorrow as in 20 years. If I had enough cash to insure myself, I obviously wouldn't need to take this losing bet, but I don't.