In practice, once the eviction is able to go through, sheriffs office gets to it when they get to it.

For more real estate focused methods and practical advice, add to your list, "Set For Life" by Scott Trench and "The House Hacking Strategy" by Craig Curelop. 

Simultaneously, I have successfully developed and managed a portfolio of rental properties in the Chicago area over the past eight years, valued at approximately half a million.I am seeking advice on how to strategically leverage my skills and resources to make a breakthrough into Commercial Real Estate (CRE).

I think you may have very well narrowed down my strategy choices down to one of three; the BRRRR method (although this might be too much to start with for a newbie), the live-in flip that you mentioned (probably the most practical as I've been part of many different projects in the construction industry), and a combination of house-hacking/live-in flip (probably the most rewarding with a potential to swap between units as I finish one in order to bring better rental income).

In my mind this negligent behavior from standard business practices has negatively impacted the operations of the property. 

This takes a long time to do right, but with practice, you can add 2-3 very thin coats of shellac over the spot without causing the treated wood to re-darken.

You asked good questions in your post and, if you take your time and really consider what it is that is important to the practice you want to build, then you'll do well. 

Whether you are a seasoned investor, a real estate agent, or someone who has successfully navigated these waters, your input would be truly appreciated.I'll go ahead and start by sharing some of my best practices.

An investor friendly agent can do all sorts of helpful things, like setting you up with a search for properties or connecting you with folks who have recently done deals like the ones you want to do. 6) Consider analyzing a deal or two in your local market, just for practice, with a free use of our Rental Property Calculator (or other calculators).

Considering your options, #1 seems like a practical choice – being transparent with your tenants about the situation and proposing a reasonable rent increase.