My wife and I currently live in a duplex with long term tenants in the other unit and we also have a single family residence that we rent out on airbnb. We have enjoyed the whole airbnb experience and have hosted guests from all over the world, but here in Indiana, we are subject to a 22% hotel tax which really hurts and makes a long term tenant seem more attractive in some cases. We have had pretty good luck renting it out and earn almost 2x more than when we rented to long termers. There has been zero damage and in fact some guests even buy things for the house and one guy even cut the grass for me. Now as far as living in the duplex...I think it's a great move, my wife isn't really convinced of the badassisty of it, but I'm sure she'll come around. You may have to deal with little issues from time to time, but it's totally worth it to live for free. I would keep the renters in there for the 1st and 2nd quarter and try to get the airbnb going for the 3rd and 4th. We purchased our duplex for just over $50,000 and it's cash flow positive with only one unit rented ($560 rent, $391 mortgage with taxes and insurance included). My buddy, who just became a millionaire, lives down the road in a duplex that he picked up for $40,000 and he rents the other unit for $650. He just started renting out one of his houses in Athens, Greece on Airbnb as well and has had good results so far. So convince your wife and figure out the situation with the tenants and then get to work collecting $ Use cozy.co, square, or venmo to collect rent from long termers. Offer your airbnb guests bikes, uber, car rental through Turo, internet access with a roku, and share some of your local knowledge on the cool spots they check out. Good luck!