Don’t trust any automated screening without verifying the data put on the application is correct. 

Is there any way to modify the driveway or utilize a different entry point on the property to make "newbies" comfortable with the ascent?

Anyway, bottom line is housekeeping inside does not have anything to do with entry points outside.

I cross check that against what my realtor and other local folks I have relationships with tell me about where the neighborhood is trending, as well as rent-o-meter and searching for high-level rental data/trends.

Proven fact backed by tons of research and data.

I would agree that general networking and education help lead you to a market,  but it gets overwhelming in where you turn to collect data from there. 

Interview the agents and get some market data to help you narrow down which market or markets make sense for you.  

Some things to think about:1) "I saw how easy it is to get a license here" - low barrier of entry is not a good sign2) "I currently own one rental in Columbia" - you have no idea what you don't knowWhile your enthusiasm is commendable, it won't pay the bills or increase your knowledge.Property management has a "million moving parts" and any one of them can trigger a disaster:(So, you may want to consider working part-time for an existing PMC to learn the ropes.Of course, you can also charge full speed ahead and see what happens...

They might not be able to give you all of the data right away, but should certainly explain the process, such as obtaining a new assessed value based on market price (your purchase price) upon sale of the property.

Realtor.com would be a good second bet since it pulls all MLS data.