Based on the new information provided by the City for what can Qualify; I would say this likely could Qualify for an Express Permit.

I have house hacked 3 times in the Logan Square & bucktown neighborhoods.It will probably easier if you can provide some more details on the analysis....maybe consider BiggerPockets calculator. 

I still have it today and provides almost more cash-flow than any other property I have.

Depending on the volume of expenses, 14 properties could easily be done in a few hours a month.

And they don't provide much info on dividend distribution. 

All the housing agencies send their voucher holders there.Just be forewarned - many S8 voucher holders don't want to pay application fees, provide any documentation, expect you to fill out their S8 paperwork (!)

I would recommend you read the book 'ninja selling,' as it provides you with a solid plan and schedule filled with action items to follow and execute to get results (if you follow it) And its not cringey, salesman strategies.

I need someone who's familiar with FL Statue 718, as well as someone who has experience in managing properties of this/similar size, is versed in contract negotiation with vendors/service providers, & is a more hand-on individual.For context, the condo already has a property management company.

I can provide you with an interactive map that meticulously outlines which streets allow for student rentals, offering clarity and ease in navigating the local regulations.With house prices and interest rates on the rise, coupled with the university's expansion, rental rates are experiencing a corresponding increase, ensuring a favorable outlook for investors.

Some of the others are sit-down PowerPoints that don't provide much value Also, go to BiggerPockets -> Build Your Team -> Local Meetups, and there are many great meetups there!