Easy way for people to put listings up?

I actually have 2 questions. Sorry if I mislead you 🙂

1 – Which plugins would allow users to register on your WP site, and put listsings/ads of a house, or other random ads (like pet sitting etc)?

2 – Is there a way to show a map of a region, where certain parts of the map, when clicked, open a list of providers (added manually by me previously)?

I hope this isn’t too much of a broad question.