I subscribed to pro as a gift to myself for earning my paramedic license.

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.

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How do I get my money back with minimal tax liability?

You will earn more overtime, 

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

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.

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).   

So I help investors in the process that lets them sell investment real estate and purchase replacement real estate without paying tax on the profit.  

My suggestion would be to come out to as many in person meets as possible (https://www.biggerpockets.com/forums/521/topics/1177645-tax-...), ask tons of questions, and figure out how to hang out with people who are doing what you want to do (add value, work for free, do anything to get that experience.What area of Chicago are you looking to invest in?