Are you generally seeing cash flow positive deals from day 1?

What you have calculated is not cash on cash return.   

Don’t forget heloc, DSCR, 2nd on primary, borrow from retirement accounts, credit card cash advance, property reserves, home improvement store credit, etc etc.

And none of that counts the 10’s of thousands in tax advantages I reap without any advanced skills or planning, the government just hands them out. 

Eventually, I’d like to start using the cash flow to pay myself and work toward replacing my day job income.

“ cash flow returns” almost always compare horribly to a simple bank CD after you deduct for insurance, prop taxes< vacancy, capex, prop management (or your personal time.) etc etc etc. 

The third property has a nice cash flow.I am wondering if there are steps I can take to reduce the cashflow issues of the 2 properties before obtaining another property, like pay down the mortgages or should I just save the cashflow from the third property to pay for any future expenses?

Congrats on your cash-flowing property in Chicago! 

So if you are anticipating higher rents and therefore higher income next year you may want to wait till then if you are trying to maximize the amount of the cash out refi.

Its being operated at STR from last 30 months with great cash flow.