This seems like an interesting concept.
I'm living in PR and usually available Wednesday through Saturday morning (if there isn't a swell on the west of the island). If you need a ride from the airport or someone to show you around, I'm usually up for an adventure.
Also, I'm up for running away to anywhere in June. I'm an outdoorsy kind of person: mountains, lakes, oceans, paddle boarding, surfing, snowboarding, scenery... that's my kind of getaway. If an opportunity to stay, live healthy and be in a positive income situation arises, I could be persuaded to do just that.
I'd really like to live somewhere that has consistent surfable waves and a friendly/involved/active/happy community.