You will likely save 6 digits on the gains as well as 4 digits (maybe 5) on property taxes annually by waiting until death to sell the property.  

Pay cash.  

Personally, if I can hold with a little bit of cash flow but good upside appreciation over time I’d prefer to hold.

What you have calculated is not cash on cash return.   

.- Would you be requiring custom changes often to your digital workflow?

Quote from @Eyad Ahmed: Starting my Virual wholesaling plan from egypt is quite challenging but doable i'm targeting indiana market with an established LLC and the deal machine software and mojo dialer and a presence whether on social media, a website,etc  looking to connect with realtors as I'm looking to start novations as well alongside wholesaling any recommendations about my plan or tips and trick's on how to close my first deal, also if there is any buyers in, fort wayne, indiana polis,munchie drop your email to add you to our end-buyers list also any recommemdations of title company that deals with digital banking for example: mercury,wise,relay and is investor friendlyI am the owner of DealMachine and also have 19 properties in Indianapolis.

“ 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.