Hi Marlena,Love the authenticity and vulnerability of your post!

Chicago's debt will make it much more vulnerable to macro problems in the economy so any national dip will impact Chicago harder than in other parts of the US that have less governmental debt and more growth. 

You are dealing with very vulnerable people.

You leave yourself vulnerable to a lawsuit if you are unable to follow through and the owner decides to sue you.

First, favorable premium rates are given to homeowners for the inherit “pride of ownership” that comes with personally occupying a home.The second reason is that when a property is vacant, it is much more vulnerable and likely to have what the insurance world calls Vandalism and Malicious Mischief (VMM).

It's a very tight insurance market right now in wildfire vulnerable areas.

Congratulations on being brave and vulnerable!

Personally, I'd be careful about inflaming the situation with attorney letters or lowball concessions. 

So the more you stick under one LLC, the more vulnerable you make yourself. 

@Jennifer Rysdam - I am speechless - really don't know what to say - I wish I could apologize for all the terrible men like that, and for that particular a$$hole - my heart hurts for you - thank you for sharing and being vulnerable - that takes a great amount of courage, and I am grateful you're still in the business - sorry, this rambling is taking me a long time to type - I am struggling to find what to say - we need more honor in the world