Where I live (or have lived). Aim to get other people to pay for my mortgages. Started out by renting out a spare room, then moved and rented out the whole property, then moved again and rented out both properties. When I started out the rent was around GBP300 per month and the mortgage peaked at GBP450 per month (interest rates were unusually high at the time), and now (after many years) two lots of rental income total approx GBP2700 per month after fees and three mortgages total approx GBP1800 per month (although interest rates are unusually low at the moment). Calling it passive as I've never bought a propery as an investment, just a place to live. Not entirely passive though as there can be a bit of work when there are problems with tenants. I reckon the hassle factor is worth the free accommodation though, given how large a chunk of people's income accommodation usually is.
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I've always thought that living my entire life "having others pay for mine" would be ideal. Rent out property, the margin pays for my own residence. Operate restaurants, the margins provide (at a minimum) my own meals. Get into the car rental business, it provides my transportation as needed...
Can't quite get myself to bootstrap this idea...