I know I need to assemble a team, I know I need to understand markets and analyze a ton of deals, and I know I need to coordinate it all for execution with the right timing.

(Note: I'm not a lawyer, but this is my understanding based on my experience)  A human being will need to sign on behalf of the LLC and that human will need to have the authority to sign. 

. - You've got some pretty solid information above and concurrence that it shouldn't cost nearly as much as you thought, but on a separate note, I'd like to understand your situation a bit better.You are currently just looking for a Chicago property to purchase and asking the quit claim question in preparation for closing? 

It's all noise because you shouldn't invest until you have a foundational understanding of what you are doing.

@Shaylynn O'Learyi understand the frustration of living in a high cost market and looking at the appealing price points in those other markets. 

It would be smart to do a full lease audit, estoppels issued, and tenant interviews.And if you are buying cash, there is nothing mandatory, since it is your money at risk. but again, physical condition inspections, understanding of tenants (they are a great source of information about issues with the property that the landlord may not know or may not disclose), surveys to understand accurate property lines, etc.

Some quick googling suggests the answer is yes provided I don't rent it out more than 180 days for the first year, do I understand correctly?

Many S8 tenants are getting free rent money, yet don't take the time to understand the program and dump everything on their caseworkers and landlords!

Depending on these answers one lender who charges 3 points could theoretically have lower total transactional costs than a lender who charges only 2 points and its important to understand all fees associated with each lenders origination process. 

I would recommend house-hacking or partnering/mentoring to get a better understanding of real estate on your first deal.