"Gambling" that the value of the asset will increase also has its risks.

Starting an S corp now will just increase your administrative burden and tax prep fees. 

This problem is..I live in the DFW area and the market has pushed prices up rather high, along with increased demand which makes it harder to sweet talk sellers into selling at a lower than market price. 

You didn't mention this, but re-financing into long-term financing will significantly increase your ROI/IRRWhat do you anticipate the vacancy rate to be?

The increase exposure on E&O is the main hurdle. 

I oversee a ~1.4 million SF shopping center / retail portfolio and from my experience here are some things I see that may help increase your odds of landing a higher quality tenant beyond the basic demographics (income, population density, etc):1. 

Every new investor was always tentative to start with and just did a small amount, but as the returns kept coming in, and they became comfortable with the process, they would gradually increase their investment over the next year or two.  

Are they looking to reassess the property for an increase in taxes possibly?

Only difference is increased bonus depreciation on equipment, but the theory and methods for everything else remain the same.

A 20% down payment would make the mortgaged amount $160,000 and your monthly cash flow would increase by about $108.