I found a property management company who got good reviews from Maui neighbors who had used them for years. When she came to visit she said she wouldn't feel comfortable renting it because it was too awesome! Renters would be hard on everything, inside and out. Most properties she rented were empty and the bare basics outside.
About the same time, a friend I met through volunteering, Lisa Lou Who, was just informed her condo rent was going to increase. Again ... every year. Hmmm ... she loved my outdoor living area and loved gardening ... if I rented to her, at HER current rate, it would cover all my costs + $800 per month. That would almost be enough to cover a studio apartment in Portland. I mentioned my scheme to her.
She would be getting a tremendous bargain ... a two car garage and more space and the outdoors of all outdoors. Electric would be $20 a month (instead of $200+) and rather than change utilities out of my name, I included them (up to a maximum) in her rent. A bit nicer neighborhood for her AND she had already met several of my neighbor friends.
I was getting peace of mind that LLW would care for things just as I would, maybe even better. I could leave everything there ... coffee maker, kitchen stuff, garage filled with the necessities of upkeep, bikes. And I could ask her for two weeks of vacation there ... as part of the lease.
This could really be a win/win situation!