@Brian Ploszay is right - Central IL isn't the most stable right now so the HUD is important.

It's extremely important to me to be able to see if tenants have submitted their payments, and I don't want to have to keep track on day 6 of who needs a late fee sent much less chase after my tenants for it. 

Area of town is important.

Of course, the quality of the works is most important because it will be my brand equity.

Karl is correct, education is the most important thing you can do, always.

Zillow, realtor.com, and your agent's MLS portal will all show you recently sold houses.Make adjustments based on size, condition, age, and any other important factors.

It doesn't necessarily not work, but you do have more pressure on your margins due to more people being involved making it that much more important to buy at a serious discount, and that is going to be your biggest challenge. 

I fully understand the importance of good screening.

A simple way to do this without appearing obtrusive or mean is to give them a letter with some important instructions for vacating.

Not only is vacancy an important matter, but also whether Airbnb will face restrictions too.