Would you be able to rent for cheaper if you didn't have the property?

Kind of Spanish looking building behind the Mexican restaurant. 

Here's some STR companies in the area that can possibly help you out...Go Wander Home Desired StaysThe Sosi

The lending type doesn’t matter.

The beauty of REI is there is no need to make the mistake my wife I  made early on thinking we could do it ourselves. 

We do, however, have to register in the State where the property is located.

I recently obtained my HI real estate license to access the MLS and assist with my personal house-hunting needs.Does anyone know of a more boutique brokerage on Maui where I can hang my license with minimal overhead and without the requirement of going through a mentorship program?

Most of them do not and can even hurt you - as your S-corp with rentals. yeah this was under the guidance of the tax professional i went to.

Mainstream homeowner policies won't cover sober living because they don't account for the risk of multiple people recovering in the same home

More states are creating "just cause" eviction laws, essentially stating the landlord must allow the tenant to remain in the property except for a few specific situations.It won't end well.