I guess I can keep my cash flow. 

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?

Also, conventional lending will NOT allow you to get gift funds OR borrow unsecured funds to help fund a down payment on an investment property.

It is typically lower than cash-on-cash and you can put it somewhere around 6% conservatively.

Congrats on your cash-flowing property in Chicago! 

Hi Lenders, currently in the market for a cash flow management tool to help organize payoffs and broker commissions to get a better understanding of how many more loans I can fund on a given month.

In the past, I cashed out my 401K(Paid income tax + Penalty).

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

I don't think we are going to be able to come up with $50K before they're going to need to move and no, definitely no family members able to gift $50K. 

Here's a guide that describes what good cash flow looks like and how to analyze a property.https://www.biggerpockets.com/blog/rental-property-cash-flow...