Help with Zoning / Permitting - North Fort Myers

[Pasquale Zingarella]

I own a quadplex with a huge end unit I am considering converting into 2 smaller units for additional cashflow. 

Bit of background - The property is in a commercial area and I believe at one point in time was a hair salon.

Given this is my first rental and my inexperience I reached out to a couple contractors and one of them told me to start at the permitting and zoning office. My questions for BiggerPockets is:

-What questions should I be asking the zoning and permitting office to make sure this is ok/legal to do?

-Should I expect push back? If so what should I be prepared with to combat?

-Should I expect anything ....unexpected....when going from a 4 unit (residential) to a 5 unit?

Any additional insight would be appreciated!!! - Pasquale