paolo "However, being "free" listings, if a member stops paying the membership, the listing will not expire." Would it be possible to somehow create an option (maybe even just a toggle) where we can link the membership to all the created listings under that one user? That way, if the user decides to end their membership, it will then expire all listings create it under that user immediately.
Fun fact, this method is straight out of a website service called investorlift. It's a real estate investing platform that allows sellers and their representatives to list as many properties as they want as long as they are paid subscribing members. The monthly cost for some of these real estate investing firms is in the thousands! But these real estate investing companies are happy to pay as long as they get leads to sell the house.