Your post reminded me of this quote that I think you capture. 

Outline my process and begin to capture my systems to eventually duplicate myself in the future2. 10X my marketing plan by sending out more letters per week.

Remember that if the tenant moves out of the property you will likely be spending thousands of dollars on cosmetic updates to be able to capture the higher market rents so it may be a worthwhile option to meet on this middle ground value for rent and keep them on a month to month so you can get a sense of the quality of tenant they are.

The movement in the market that they can capture is the "Cap".

Be sure you have a completed move-in inspection check-list and do periodic inspections during tenancies, so you have something to compare against after the move-out.We also use a Return of Possession form, which makes it clear the property is back in our possession and captures the tenant's forwarding address.

When we had bedbugs show up in a unit, what they told us was the tenant had to capture one or kill one for them to be sure that's what the problem was.  

You may want to consider reaching out to your State Bar's Lawyer Referral Service found here: http://www.illinoislawyerfinder.com/find-a-lawyerOr, alternatively, you can ask your Creditor's Bar Association located here:http://www.ilcba.org/There are two kinds of Debt Collection firms; large "captured firms" that handle only major clients, and then small shops who handle solo clients like yourself.

From your examples, the potential missed rent payments (due to Coronavirus) and CapEx over the years, should have been captured in the estimated monthly vacancy and CapEx.  

Another improvement for the owner is putting in meters or setting up a RUBS program to capture and make utilities a recoverable cost. 

@John Faraday it seems that you have great experience and a system worked out to capture value/minimize cost along the transaction process.