We did $50 plus $10 every additional day after the 5th it was late.  

However, DSCR requires you don't live in it so this is not an option on the primary. 

It also depends on the cost of adding the additional bedroom.

I used to live in the Indy area so I was familiar with the city and much more so now down to a detailed level.

Additional problem - they have been renting the bedrooms out to dormers.  

I can't say whether or not hiring a property manager would be better for you - not sure where you live and if you have the ability to find maintenance/repair people in OK easily or not. 

The basement meets all the criteria for a dwelling unit in Chicago, but we need to go through the re-zoning process.In addition, we have old R22 forced air units that we want to replace with a heat pump.

Anyone else hear of passed legislation mandating the property managers in addition to property owners are now responsible financially for any repairs not done on properties, taxes not paid and rental certs not submitted/paid for, lead based paint fees/apps and required work, HVAC certs every year and proof utilities (water/sewer) as paid, and general compliance matters?   

Additionally, provide guests with the app and access code programmatically before their arrival date so that they can access the property.

A bookkeeping professional will "translate" the PM's data into your master accounting platform each month so all of those transactions are accounted for.This allows you to see how your business(es) as a whole is doing financially in addition to how each property is doing.We actually catch a lot of mistakes doing this for our Clients as an added bonus.