If it's not draining completely, or not running the full spin cycle they could be starting out with excess water. 

I don't have anything but empathy for you and a tenant that's clearly heading to the curb.Maybe adjust your future leases -- Is there a regulation/law in Chicago that would preclude 'refunding excess rent'?  

Also, make sure you completely understand what the umbrella coverage is providing excess coverage for/over. 

Also, make sure you completely understand what the umbrella coverage is providing excess coverage for/over.

I realize now that there is excess, for me, and for those around me!

My favorite line "excessive stimulus has a way of covering up problems."

I ended up putting down 10% on a 2 bed condo in South Boston and using my excess cash to buy a cash-flowing asset outside of the city with a 25% down commercial loan.

One of my goals is to deploys excess capital and put it to work. 

This was done by any of the following; a statement showing the down payment transferred “outside of closing”, funds transferred to the title company as a down payment but actually from the seller, the seller “purchasing” another asset from the buyer for a heavily inflated price, the reported price being in excess of the “real price” with the seller taking a “silent” second, and something known as “disappearing” earnest money, “paid” directly to the buyers attorney.

I agree that it is the tenant's responsibility to get the rent to you, but given the circumstances involved and the fact that she is making a real effort to get you paid, I don't think a 25 minute drive is excessive.