I grew up in a very wealthy area with huge houses, many with pool houses that had bedrooms. I started housesitting in the summer when I was home from college and had couples/families who I sat for regularly. At the end of the summer, before my sophomore year, I sat for a couple, in their 40s, who were both hot as hell. They said they both traveled for work a lot (no kids) and one or both are often gone a couple of days a week or sometimes over a weekend. They wanted to know if I would be willing to live in the pool house the following summer so I would always be available if they would both be gone.
They paid more than any of my other clients and were really nice. They always had the fridge stocked with my favorite food and drinks and didn’t mind if I had a friend or two over while they were gone. I was also single at the time and didn’t expect that to change anytime soon so I figured, why not.