They handle payments, payoffs, and year-end tax information. 

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.

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

Unlock financial peace with Rapid Fast Cash! Trusted for years, we specialize in expert tax consulting and services, including swift tax refund assistance. Our year-round availability ensures tailored solutions for ba...

Unless I'm missing something, the property(ies) you are purchasing is a liability, not an asset.

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).   

Unbelievable • His insurance won’t cover because as it turns out commercial liability does not cover craftmanship defects they need E&O insurance for that, hard lesson learned, 95% of small contractors will not have E&O, it's an extra cost for them and only the larger construction companies carry it.

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?