Quote from @Robin Simon: Quote from @Jonathan Greene: To me, cash only is just cash.

In 20 years, those same houses that you own today will be paid off and worth double what they are now. 

If it takes a year I am not sure if it's worth it.Thank you No program is worth $10k, everything you need or want to know is available for free already.

Looking my insurance policy it mentions that I can opt for settlement under Actual Cash Value vs Replacement Cost. 

The amount of equity I call pull is less than the cash I have but not significantly less.When doing this analysis it struck me that it may not be worth using a HELOC for the simple fact that the interest rate is ~9%* while the funds in my high yield account are only yielding ~5%*.

Worth has tough restrictions, Dallas and Plano I think are both trying to implement restrictions.Where do you want to buy?

If you want to put down a low down payment, you might not cash flow for a few years.And FHA for 3-4 units is almost impossible.

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?

With land investing/flipping becoming more democratized/accessible  (so many landed courses, tools, resources etc), current prices/RE trends etc, is it still worth getting into land investing/flipping for a brand new RE investor ?

Congrats on your cash-flowing property in Chicago!