As others have pointed out, you are actually in a great position!

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

I noticed on the city website that it can only be done in certain areas, which I'm more than fine with.

If you are not going to leave there at all, and you can't do Bill 23 or have any value-add to get to positive cash flow, then NO, don't do it. 

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

If you rented this home and it was putting $3K positive cashflow yearly in your pocket, the returns would be 3/4=7%.  

The judge had doubts about the veracity of the website I was using to collect the rent (I gave him a print out of the payments and non-payments from the website) and thought we should have driven to unlock the door for the tenant when he locked himself out (3 hours) instead of telling him that was his issue and he should call a locksmith.In the end the judge asked him how much he thought he owed us and he did his calculations in the courtroom, not having this prepared. 

Lastly, if the tenant does become delinquent and we have to file a claim with Rhino Insurance to collect their deposit, we're adding to the financial woes of that tenant and putting them into an even worse financial position when they wouldn't have qualified in the first place.Thoughts?

I have a hard time visualizing things myself so using Alex has been a god send, here's her website https://www.cheatsheetdesign.com/ It's around $400 for her help and personally is worth it to me just to save my time!

Does physically going to downtown reveal more info than the Cook County Circuit court website?