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.

Solutions: expand National Historic Rehabilitation Tax Credits, preservation tax credits, save the historic and as Baltimore likes to call it charming housing.

@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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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).   

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

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.

Hi All,We have a prospective tenant who says they are self-employed but don't have any tax returns for the past 3 years.

Does anyone know with the recent Tax Cuts and Jobs act for 2024 if bonus depreciation of 100% has been extended to 2026 for short term rentals? 

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?