Would love to hear what you’re focused on or planning!

I’d also love to hear your predictions for how the real estate financing landscape might shift this year and how you plan to position yourself for success.

If you plan to live there in the winters, you might have a hard time doing long term rental outside of that and finding a new tenant every summer.

I used to work in Planning & Zoning. 

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

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

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.

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.