Our current mortgage terms include a late fee after 5 days, so they’re already paying extra each month and have to split the total monthly payment up between 2-3 payments when they get their pay check.

As far as credit, you would want a score above 680 ideally to get the highest loan to value on a cash out refinance, but I would aim higher at 720+ as that comes with a significant rate drop.

I cash flowed that house 500 a month. 

The cash flow does improve with the hold .  

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?

Quote from @Scott Cash: I'm part of a three-member LLC that owns a $10M commercial property outright (each holding 33.3%).

I use cash comps as the first people I look to sell wholesale deals to.  

@Jacob Glover seasoning period on a cash out refinance for a new construction property starts ticking from the time you took ownership of land with conventional financing, but requires 12 months seasoning. 

So you use hard money or cash, fix it, resell it...and try to resale fast. 

@Shaun OrtizMy first deal 19 years ago started as kind of a mess, but I got it cash flowing after a few months.