The good news is that the entry point is much lower and cash flows the best. 

Then determine your strategy - cash flow, appreciation, tax deferral.

You also described them as an investor, not a successful investor.In the current market buying move in ready property with conventional financing at high LTV is not going to generate good cash flow regardless of what RE agents in the Midwest may state/imply. 

My low ball offers take things breaking into consideration so I’m ok with some issues that come up.

Two of those units should cover all your expenses and give you pretty good cash flow, but that depends on where you purchase the property as well as condition.

I'm looking to sell a portfolio of 12 cash-flowing properties in Ohio valued over $1 million in total.

The property is 50% vacant so the cash flow out of the gate is severely negative (I'm guessing).

Letting old tenants stay for cash flow while we got engineering and planning done was a challenge.

Then whatever is left over is the cash flow that you can use to build up some reserves with and eventually take as your profits!

We are hesitant to give up a predictable income and steady cash flow.