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It's our first time setting up a medium term rental and bought a house with 6 bedrooms that the previous owner had been renting out as an MTR for travelling nurses (by the bedroom).

The HOA is money hungry so they will never ban short term rentals. 

I am also probably not buying anymore in the near term because I can get similar returns from the tech monopolies without the work.

It spells out the monthly rent,when it’s due, the length of the lease (or term), should contain clauses required by the federal and state governments, andmuch more.

In the last 6 months i've acquired two more short term rentals in the Poipu Beach area and completed a 1031 exchange.

We also try to identify hot prospects in areas subject to waitlists for those that intend to personally utilize the property for vacation usages or rent mid term (30+ days) until a permit can be secured.

I know that many in the bigger pockets community are more the DIY type and self-manage, but for those of you who have used property managers for your short term rentals, what have been the pros and cons of your experience?

This is just the price of the option and I prefer the term because deposit often carries other definitions and expectations.

All of those are "part of doing business". 3 years, 7 Airbnbs and hundreds of guests later I'm still a proud host and a big fan of the mid-term / short-term model!