I personally do not think this is necessary if this is a portion of your primary home.As others have mentioned, i would connect with your insurance broker and let them know exactly what your are doing and what you want coverage for:- if i rent a portion of my property our on airbnb for a period less than 30 days and that guest is injured on my property, do i have coverage?

The added units that I own also has no firewalls to the adjacent legal units, and no ones been injured.

I mean this liability insurance is in regards to the property and someone being injured/killed.

In CT, if an employee is injured and his/her employer does not have coverage the claim moves up to the firm that hired the employer.  

Also, what happens if your tenant gets injured inside the unit (god forbid) and they sue you because you allowed them to live in an 'unsafe' unpermitted home.  

I am trying to understand why is it that I might be held liable and dragged to court if my tenant's aminal injured someone.

Just something to think about.Slip and fall cases are very difficult for an injured person to win in Illinois.

They didn’t pay for November and called me in crisis mode saying husband is injured and couldn’t work, they had to get a new health insurance plan, car repairs, all stacked up.

Long winded goals shortened, I will be done with pay checks in 3 - 5 years and live off rental income, 8 - 10 years have a large excess of cashflow most people would squander, take 5 years off to travel then come back and start a non profit funded by my rentals that designs and creates prosthetics for injured animals.Most of my friends and my now ex gf would role their eyes at me when I would talk about my goals.

If someone injures themselves and sues, they will be suing the LLC and not you personally.