I know plenty of people who own multiple houses. And plenty of houses that get rented and paid to the owner/landlord.

Insurance is not free money its a pool of money gathered from monthly payments together to offset risk. You don't need to distribute the risk over all of your homes you buy a policy for each home.

This stuff is 101. And works all around the world. There is even an app called airbnb that will find short term rentals for your house.