In terms of educating yourself, it would be good to get an understanding first of what, if any, your family's estate plan is, and if there is not a good one, get yourself educated in that area for a continuing discussion with your dad.

I understand some of the basics of real estate but there is a ton I do not know.

I understand the costs associated being an Agent (I actually took a course and passed the licensing exam a few years ago, but never did anything with it as I started a new career as a Firefighter). 

You just need to understand the demand in any particular area you're looking to invest in.

Essentially what I took away from her explanation was, a lot of owners don’t want to fool with the county on things like this if they don’t have to, which I can understand.

If you already own it and it was a personal residence that you don't want to sell providing you live somewhere in the area, have an interest and understanding of your local rental laws and aren't in California (the laws) or Florida (the possibility of assessments) then self management is a possibility. 

If the newbie user can't explain or doesn't understand the data, then they know they have an educational video to make.

Up to this point we've managed it on our own, but we are entering waters we don't fully understand how to manage. 

It has made a huge difference for me understanding my data and I have nothing negative to say about it at all. 

With the right approach and a solid understanding of the market, you can find great opportunities for success in the Midwest and beyond.