Or in other words, the rent received from house hacking would cover our housing costs (mortgage, property tax, insurance, repairs, utilities).Upon research however Oahu seem to be a high cost and low cap rate area similar to SF where we currently live.

With that loan product, they will not be looking at your DTI or work experience and will qualify the property based on the DSCR (Debt Service Coverage Ratio), which is a measure of the property's cash flow.

If you don't have any debt, a 750+ credit score, and income, you should not have any issues being approved for a mortgage. 

@Brian Burns You could do things this way, but it will be slooooow and taxes will eat your flip profits alive!

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It depends on the type of loan, loan to value, fico, income, debt, and experience. 

If the client is self-employed or they own other real estate, you'll want to ask for a copy of their two most recent Federal tax returns - all pages/schedules (you shouldn't need the state tax returns).   

Investments in Opportunity Zones can offer great tax benefits, but when combined with a cost segregation study, the benefits can multiply.An Opportunity Zone are areas that struggle with poverty and lack the necessary access to economic opportunities.

Is there any advice you'd give me on our particular situation:Husband and I are 50-something "millionaire next door" types with no debts and significant savings.