If there are any lease violations, send all tenants a Notice to Cure and start the eviction process; lease violations are not part of the moratorium.About the remaining tenant, she doesn't qualify to rent the property on her own. 

I guess price has gone high while rent remain low.

I can't comment on whether or not any of that will reverse but I will comment on is that as long as Chicago has the following it will always remain a place for commerce which then supports Real Estate.

If there's no convincing you to remain a landlord and shift your sights to a turnkey provider like REI Nation, the next best thing is to invest in an index fund like VTSAX.

Otherwise, I would look at getting a job that ties you to real estate and allows you to stay in that world...

Neither will have mortgage insurance, although it's probably tied into the higher rate. 

From the sounds of it, he doesn't have a job, so no ties to the area. 

It remains however I want to ensure the happiness of my friends and family as well.

AC breaks).Regarding your second questions, I would restrain yourself from tying up all that cash on another project for the reason I mentioned above. 

There are currently 7, in the process of selling one to help get this mess sorted out and invest back into the 6 that will be remaining.