At the time of purchase, I knew I might not want to stay indefinitely and at some point to might convert the home to a rental property.

I know you want to go full time and jump in, but I'd recommend staying with your day job as long as you can - it makes your life a lot more comfortable to have a steady stream of income to pay the bills every month!

.✅ Knowledge of Chicago Rental Laws – A good property manager stays up to date on local laws, helping you avoid costly legal mistakes.✅ Maintenance & Repairs Handled – No more emergency calls at 2 AM about a broken water heater!

If the best you qualify for is alternative financing when the purchasing loan matures you will  likely be treading water barely able to stay a float. 

I'd recommend staying within 10-15% of the median priced home because that's where the most demand will be not only for renters but owner occupants as well. 

Existing tenant stayed in my rental property 3 years without rent increase.

I have 3 windows as well that don't stay in the open position that I have to replace.

Because that is when the impacts are most felt of everything one has to do with the now pile of ashes. 90 days to do nothing forces people to engage with staying. 

Professional property managers stay updated on legal requirements through memberships in state or national organizations.

Does she have any legit habitability claims to sue for, especially since she claims to stay in hotel now?