Additionally, if you got a loan on top of your cash advance (say, you only had enough cash for a down payment) then I imagine you're also paying loan fees twice.This may all be fine and dandy if the numbers work, but is this a viable plan or a total gamble?

Make sure you decide to concentrate the one you planning to do. 

I am a first time homebuyer looking to house hack in Chicago and I have an almost 800 credit score, but I don't really have much saved up beyond my emergency fund for a down payment.

Why not just find a high yield savings account or invest it in the stock market?

So if you plan to take cash out and not "Sell or take more cash out" in (X) years.

Is there any website i can use to find a floor plan of an existing house even if i dont  own it?

We plan to do a cash out refinance and keep this as a long term hold.

Outline a business plan, put up investment criteria, creating financial system and invent property management practices.

Planning to talk to owner.

But while the plan was always to house hack, I didn't spend enough time looking at what would make the best rental.