The buyer can obtain a property with no mortgage qualifying and or a lower than current interest rate, or on terms not readily available otherwise.  

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.  

In a slow market homes sit and rot, they are on the MLS forever and the longer it sits, the lower the price goes to find the sweet spot for just the perfect buyer.

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

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

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.

you have to also classify what do they do for a living those of us that are Real Estate Professionals and taxed as such to most its a lifestyle I know it is for me.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

In addition lower rents will decrease the value of a property, not necessarily its appraised value, because no buyer will desire to pay retail for properties with reduced cash flow.