Really know your area and the ARVs.

I know I have more questions but I've drawn a blank...

Not everyone is fit to be a landlord and I don't know what expectations were set when you first bought it.Regarding him not working on the house since he started dating someone, you need to politely tell him that he has obligations that he committed to.

I know how tough it can be balancing projects in different locations. 

But I don't know what these late payments/fees, etc are.

Do you know any investors in Chicago that are willing to connect? 

A very important note to your getting started phase - No real investors want to "to grab a coffee or hop on a call" without getting to know a little about you and knowing if you have something to offer them.

So to that end even though I think of myself as private I am in the business so I am a HML  the other folks posting on this site are all HML.. to me a PML is just that someone who is private and NOT in the business they they do a few deals out of their IRA for solo k a year and generally to people they know..

My Milwaukee clients aren't using that method, but as you know it can help with closing deals quickly.

This flexibility allows investors to move quickly and adapt to market conditions, making it a valuable tool for real estate deals.Let me know if you’d like assistance with your financing options!