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

$500 per day penalty up to $10,000 and up to 2 years in prison for willful evasion per entityNo cap on the amount of entity penaltiesCheck with your CPA, Tax Advisor or attorney on this as it is a freight train of compliance coming!

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?

Ask yourself, why would the federal government pay MORE than market rent and waste our tax dollars?

Brandon Turner's Rental Property Investing book is an excellent primer to understanding the happy path for purchasing a property - however in this market it really comes down to having bulletproof assumptions on rents/taxes/R&M/etc. as with rates as high as they are/inventory as low as it is, there is less cushion in your returns if you analyze properties with bad assumptions.

We both work in finance, so we’re pretty comfortable running the numbers.Our combined W2 income is ~$350K, and I work remotely with a very flexible schedule.We’ve saved over $200K across various assets (stocks, crypto, cash), and we live frugally, saving around $100K a year after taxes.

Sure, but again securing $500,000 isn't difficult.That said, liability coverage is lawsuit protection coverage just like it is for you. 

Compare this to your total monthly costs, including mortgage, insurance, taxes, vacancy and maintenance.

You have to adjust your expectations to match current reality, which includes higher mortgage rates, higher prices, more expensive taxes and insurance, more competition, etc.