If your looking for more protection then just get an umbrella insurance policy, this will add even more coverage for your protection which is what people are thinking when going the LLC route.  

I may chose to have the LLC taxed as a S-Corp and then created an umbrella company as well.- Personal and company asset protection. 

I do think you would be okay with not getting an LLC and just getting a solid umbrella insurance policy, but I'd definitely consult with an attorney

I want to have the property held under the LLC for liability protection but I may have to go with an umbrella insurance policy instead.

My plan is to:1) Pay off my mortgages using the cash from the investor2) Record the house deed under an LLC (currently it is under my name)3) Bring the investor as a partner into the LLC with 50% shareI am aware of the following challenges:1) The insurance policy on my rental homes is extending liability from my primary home - I am getting an umbrella policy.

While you're at it, you might have your agent quote you for an umbrella policy too. 

Grouping properties for insurance/umbrella coverage can factor in.  

I am analyzing potential properties through the BP analytical tools and often feel I need a better umbrella overview of the Chicago market to then narrow down to witch neighborhoods I feel best investing in being a new investor.  

Personally I just keep things in my name with an umbrella insurance policy.

If I could summarize what is most important (unsolicited advice here): (1) Do not put the rental on the market until it is 100% ready for move in (2)  Provide a list of written and minimum qualifications the applicant must meet  (3) require the tenant obtain renters insurance (4) execute a strong lease (5) have a list of trusted and licensed vendors (6)  get good landlord insurance and possibly umbrella insurance if needed (7)  be quick to take care of work orders (8) let the lease dictate your actions/responses......