I currently have a duplex in Milwaukee and am living in a single family home that I plan to turn into a SFH rental.

How are you planning to scale your business or portfolio?

Are you planning on staying in that area?

If you choose to move forward, I recommend having a backup plan in case Hawaii outright bans STR.

Unless you negotiate a new contract or addendum with your PMC, they do NOT have to abide by any requests/demands you make that contradict what's written in the management contract.If they have in fact NOT followed the terms of their contract, then you'll want to send them something in writing pointing out the specific language in their contract that they violated and ask what they plan to do about it.If they fail to correct or address the issues, then you'll want to start looking for a new PMC.

The underwriter will just want to verify that you won't live in the property you are planning to purchase.

Now I am brand new to real estate so this could be dumb but I'm reading Brandon Turners "Rental Property Investing" book and I was intrigued by chapter 3 where he list out 4 plans to start with when getting into real estate.

Red flags for me include people who are overly optimistic without considering risks or those who don’t seem to have a clear plan for their contributions to the partnership.

They are holding the proceeds from my sale and I am planning to buy a couple of DSTs shortly.

My plan would be to use the equity loan from the second home to purchase another great deal (3rd home) and use the rental income from the second home to pay towards the equity loan and then start renting out the third home to get rental income and start paying off the mortgage on the 3rd home.