Become a Property Caretaker
Especially if you have some level of flexibility in your career and family life, you might consider becoming a property caretaker. People with vacation homes, those who travel frequently or someone with a large family estate frequently hire caretakers to live on and look after their properties. Obviously, becoming a caretaker requires moving around frequently, since often assignments are short term or seasonal. But, caretakers often live rent free, or at least pay very little for rent [source: Freedman]. Since people who can afford to pay caretakers are usually well off financially, the accommodations can be pretty impressive [source: Freedman]. Imagine spending your days living in a millionaire's beach house, or on a quiet country estate with acres and acres of land. On the down side, you might have to do a little singing for your supper. Usually, caretakers have some other type of work they need to do along with living in the house, like yard work, repairs, or taking care of pets or livestock [source: Freedman].
The even more adventurous might consider "workamping," a more outdoor-oriented version of caretaking that involves taking care of fair grounds, parks or amusement parks during the off season. But those who don't like to rough it need not apply. Workampers usually camp during their assignments, either in an RV or on a designated campground [source: Workamper News].
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Most homeowners insurance won't cover your home if you're renting it via sites like Airbnb. HowStuffWorks looks at insurance policies that will.