I understand the challenges you've faced when navigating the lending process.

I'm actually in the process of doing a cash out refi for this property with a few more properties I own into a portfolio loan.

Rather than spending all the money to furnish the unit for it not to be successful... and have to sell or put all the furniture in storage and create another expense. 

Would hate for you to get to the same situation as we did where we paid hundreds for appraisal, let our bridge loan tick away for weeks leading up to refinance, and only find out this info at the end of the process where we get our rates switched on us.

Any tips or advice from anyone familiar with the process would be great.

If she puts up a fuss about where she will live, tell her she can shack up with one of her drunk friends.If she doesn't want to leave, then hit her with a formal notice of termination and start that process.

Hi, I am buying a house in South Phili for a short or mid term rental.Anyone has an idea about how hard to take the license and general process and period of the licensing from the town?

That's what I would do (and have done), and it's the much safer bet, with a higher probability of success. 

I am currently in the process of figuring out the exact same thing, what I suggest is do lots of research. 

Start by educating yourself online or through courses on the house flipping process, renovation costs, and market analysis specific to Chicago.