Process is simple. 1. purchase contract2. send contract to title company3. bring cash to closing and you're done

Congrats on your cash-flowing property in Chicago! 

I guess I can keep my cash flow. 

My father and I just paid cash for a little less than a 2 acre lot in Summersville, WV.

My question is, do I just not touch the first property, use the cash flow to reinvest and pay down the mortgage or save up for a downpayment down the road OR do I pull cash out of the first property to buy the next property?

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

The issue is his definition of cash flow. 

What you want to ask is what is a good ROI or better yet, your Cash on Cash Return.I know someone who has $3000 per month cash flow.

There will be multiple markets you can achieve a 7.5% cap rate especially if you're buying with cash.

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