Are Vacation Rentals a good way to get started in investing?

@Paul Shannon across 6 vacation rentals and 2 markets I have never had a cleaner just “miss” a clean unless I screwed up the calendar on my end. Most cleaners will have a few colleagues or family members that they have for coverage should the need arise.

As for handypeople, you DO want to keep a list of 2-5. If something happens and your favorite one is on a project, then call the next one on the list. Handyman needs don’t arise as often as you are fearing. It’s definitely good to be over prepared, but self managing is a lot quieter than the limiting belief of “I don’t want to invest in short term rentals because I don’t want to have to deal with calls all the time” suggests. Is it work? Yes. Is it easy work that might take 10 minutes out of your day max most days? Also yes.