And if you are need of MTR management services, my company, Island Stays Hawaii, provides premier STR and MTR management services.   

We recently started a Co-Hosting business and are managing for one other person.

Could it attract squatters, or is it the right move for responsible property management?

Metron and Southern Water Management are two that we've been talking to.

Or subs or property managers who run off the rails. 

Every market in residential zoning has an expiration date, we just don't know what it is yet.The obvious solution is to buy in already regulated areas with tourist/commercial zoning.The returns are lower, but at least they can't go to zero overnight.

Have you considered investing in any other markets and how you plan to manage the property? 

If you can't manage what you currently have, you won't manage additional income from investments.

Let's you prove yourself to your investors in a more manageable way.  

The main downside is being dependent on the HOA—issues like poor management, rising fees, or unexpected assessments can hurt your investment.