After this tax year, I will know exactly what I need to do to progress.

Also the school districts have been increasing property taxes in A LOT of investment properties thus eating some of our profits. 

However, it must not have been your or their intention to avoid tax. 

If your goal is cash flow, then your best bet may be to live in it for 2 years, and then take that tax free gain (250k single person, 500k married) and buy elsewhere. 

It is my understanding that people refinance and then use those funds other ways (personal living, investing, some to buy another property) as a means to minimize tax obligation. 

Insurance is just an expense to factor into your underwriting just like property taxes.

Aloha @Daniel Kam - most of Kakaako has a 180 day rental minimum, so if you haven't checked with your building association, I recommend you verify what the minimum rental period is for your building.If you are allowed to rent for less than 180 days, you will then need to apply for a GET license, and well as TAT/OTAT and pay the appropriate taxes on a regular basis.  

Like your post title suggests, you die to avoid the taxes.

If you have high holding costs (financing, taxes, insurance, utilities, etc.) the longer you are holding the less money that you are makingSelling profitably - How long will it take to sell?

But given my parenthetical statement, and this shows where perhaps you may have less experience in the STR world, for no valid reason, your preferred platform can make a unilateral, unfounded decision to ban you and there goes your business.Which brings me to my final point.