I live in a gated community where everybody is a dog owner, they all roam free most of the time. It's pretty awesome. We also have a whatsapp group with all neighbours, so when we want to know where they are, all it takes is a quick message into the group and the current food dispenser of choice will let us know.
The best thing about that is that we can also just travel for a week or two without bothering. Our dog prefers to sleep in our house, so the next door neighbor will open the door at night & then let her do her thing the next morning.