On top of your career, REI and everything else does anyone else have these desires?

While you might have no desire to self-manage or to have a different company in mind, know that things can change.

C-class- These properties are typically much older than 20 years and are located in less than desirable areas.

The areas they are proposing are exactly within my desired neighbourhoods.

Your question about whether you should fix-up to sell, or sell as-is, isn't quite a cut-and-dry question as you're desired timeline to sell and your available cash come into play.  

Do to her age and desiring to be hands off, she has kept the same family in the property for nearly a decade at 1/4th the market rate.

All were surprised there's a desire to create a HOA.  

I am looking into doing business in Chicago because my father has a contracting business up there and would like to help him expand it and ultimately grow this empire that everyone here i'm sure desires.

Let me add that he is a fanatic about maintenance, etc, and his units are very desirable.

and start with making sure the lender can meet those needs or at least verify if they'll consider your desires as important.