I use mine for storage of beach toys, drying rack for swim suits, storage of extra supplies and on occasion it’s an extra parking space.  

A 30-year fixed rate mortgage is currently sits around 6.15% interest:All else being equal, lower mortgage rates reduce the cost of ownership and, thereby, allow more people to afford to buy.

Making the basement a legal unit is costly but can be done as an ADU depending on your exact location (ADU zone maps are on City of Chicago site).

Something that hasn't been brought up is the no money down dreamer who is just starting out with empty pockets.

I would not put "before pictures" that are ugly, because people cannot unsee things and usually have no imagination about what it could look like. 

Tenant shall pay for all costs associated with remediating pests from the Premises and shall inform Landlord at first sighting of any pests in order to avoid any infestation of pests.

Taxes were half paid in 2012, nothing in 2013, and 2014 has no record of payment. 

I have no idea where to start.

All improvements would be added to the cost of your property and depreciated over 27.5 years.Any interest or taxes paid on the property for the full year are fully deductible. 

Go under contract with a ~45 day closing, rehab for 30-60 days (costs wrapped into the loan)..during this time you can market for tenants, then move in.