If they decided to scrutinize such a deal, they would look at the facts and circumstances of what is being done and determine if any direct or indirect benefit has occurred.  

ZechariahUnderstanding commercial has nothing to do with residential real estate.Some small brokerages handle mom and pop type commercial or raw land but I do not consider that commercial as they are mainly residential in nature.Large commercial firms will put you with a team and a senior director that will train you up under their decades of guidance to protect the client while you learn.

Who is on the board of directors? 

The Tenant is required to obtain his/her own renter’s insurance policy against fire, theft, or other disasters, as the Landlord carries insurance on the building(s) only. .The Tenant hereby agrees to indemnify, compensate and forever hold harmless, the Landlord, its successors and assigns, any parent affiliate and subsidiary entities, their insurers, their assigns, their successors, their legal representatives, officers, directors, employees, agents, or any others who may be acting on behalf of them from any and all claims, damages, actions, causes of action or liability whatsoever, resulting from or arising out of injury to or death of any guest, agent, employee, licensee or invitee of the Tenant in or about the Premises, or damage or destruction of any property owned by the Tenant or any guest, agent, employee, licensee or invitee of the Tenant, unless such injury, death or damage solely and directly results from the intentional or grossly negligent acts of the Landlord.

I am currently working as an IT Director for a financial institution.

they might want to consider a 1031 and then contribute the property into a Family Limited Partnership and create a board of directors to handle the investments.

One important step for you to take would be a discussion with donna (lower case "d" is how she spells it) Hicho, the Executive Director of Greater Linden Development Corp. 

Officers and Directors can be personally liable for their acts, jointly or severely, including the Holy Grail of business entities, the Non-Profit!

The term “broker” also includes any person who is a general partner, officer, or director of a partnership or corporation which acts as a broker.

Go to their meeting, talk to the directors and old-timers.Also, just FYI.