Since this is something that is best done with a team of experts that know a lot more than I do I am putting this request with help from the bigger pockets community to get me started on my road to success. 

For the HVAC, I'd just question if that's the correct and best way to go about it, but I'm not an expert, but certianly you won't get interest listing a unit for rent or sale without HVAC.

You may want to work with an experienced contractor and/or other experts who have done this in the past.Disclaimer: While I’m a licensed attorney, I’m not your attorney.

One of our local real estate experts is a big fan of Lee Arnold an his system.

@Kris L.I would connect with @Josh Green, I would not be surprised if he dealt with a transaction in your neighborhood and he is a local expert on all fronts.

But if they gov't changes to a 90 day minimum, you would have to operate as a 90 day rental or longer.And talking to local experts, if you want to own a STR on O'ahu, your safest bet is to buy a unit in a Condotel that is located in the "Resort" zone of Waikiki.  

Do you currently work with an expert CPA who is helping you maximize tax breaks with your real estate investments?

Get a small MF you can house hack and start that way.I'm not an expert on the auction scene, but, from what I have read, that is a challenging first step into investing. 

Work with a tax expert and real estate attorney to finalize the deal and navigate zoning or financing complexities.This post does not create a CPA-Client relationship.

What makes you an expert that the unit is in a great location & condition and the market is hot, relative to the property manager?