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

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

Never invest in any city on this list of the 50 most dangerous US cities.Low operating costs: High operating costs are one of the driving factors for many companies, leaving states with high taxes, regulations, and other costs.

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.

@Greg StrunakA good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

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.  

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.

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.

@John BowensAre you loaning from a pre-tax 401K or did you convert to Roth and then loaning from there?

Since tax bills are for entire parcels (typically, though not always) then it is highly unlikely that they somehow segregated the taxes for that small portion and paid it.