We own a place in Maui and STR it. It’s a dual purpose play for us as we’ll retire out there in a few years for half the year and continue renting it out the other half. In the mean time we stay there 3 or 4 times a year now and do normal maintenance/upgrades while out there for not only tax purposes but guest experience.
We have a very simple philosophy and we state it on our rental page, “If it’s not good enough for us it’s not good enough for you as we all use the same stuff!” We respect people spending their hard earned money on our place and want them to enjoy it, we’d be horrified if something we did, didn’t do, or missed affected their enjoyment of it and the value they should be getting.
We respond within minutes to inquiries or questions, have good communication and make no money on the cleaning fees or tax collection. Check out consists only of optionally bringing out the trash/recycle and starting a load of laundry before leaving, not required however and they’re told so. Helps the cleaner on same day turn around and they appreciate it.
We’re 2600 miles away in WA State so proper planning is important. First is have a cleaner you can rely on and trust, this is the single most important thing if you’re not close by. Have a local that can help with immediate unforeseen issues if it can’t wait and affects the guests use of or security of your property. Be up front about the properties offerings and drawbacks (if any), communicate clearly and ensure through your listing and words they feel like you give a shit and aren’t some dollar chasing slumlord. Do these things and the reviews will reflect it and so will your bookings.
It would frankly all be far easier if I didn’t give a shit and let the chips fall where they may as long as the money keeps flowing, but I’m not built that way. Call it karma, respect or just plain old self interest but it’s paying the freight 100%+…