Quote from @Henry Clark: @Michael PlaksIf they want to stop money laundering and funding terrorism they can control the border.  

People will start to realize that a law designed to protect against criminal international money laundering captures more innocents than anything. 

What you have calculated is not cash on cash return.   

And I seriously doubt any non profits are money laundering, but then again neither is Joe the Barber LLC or Betty's Property Management LLC (which, especially if they are Single Member LLC's--which flow to the 1040 without any tax return for the entity--are already identified to the government computers at the IRS.If you want to swim with the big fish you have to get wet.Maybe the resident agents will offer to fill this out as a service for $50 to $100 (???)

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.

“ 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. 

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

Cash flow is hard to come by and I have considered looking elsewhere in more affordable states.