I say 99.9% because I don't represent 100% of the insurance carriers in the US, so there may be one out there that has unique language in thier policy, but this is the standard practice.

., for an emotional 103 support animal or otherwise knowingly and willfully 104 misrepresents herself or himself, through conduct or verbal or 105 written notice, as using an emotional support animal and being 106 qualified to use an emotional support animal commits a 107 misdemeanor of the second degree, punishable as provided in s. 108 775.082 or s. 775.083, and must perform 30 hours of community 109 service for an organization that serves individuals with 110 disabilities, or for another entity or organization at the 111 discretion of the court, to be completed in not more than 6 112 months.So the real teeth is to require that the certification must NOT be provided by health care practitioners whose  purpose is to provide certification for ESA for the individual in exchange for a fee AND if found misrepresentation it will require 30 days community service.I hope it gets passed soon.

Because of that I was approached by someone who was in a very unique situation.

A local landlord tenant legal aid organization may help them.

Max out the number of people you can get comfortably sleep there, make the property nice and unique, and get as much money as you can for those 8-10 weekends/year that really matter. 

You may need to seek the assistance of a tenant advocate organization in your area or an attorney.

Do we have to go though a financial organization, like sense financial?  

Should I put a lot of money into high end or unique upgrades that will make my rental stand out?    

People are complex, unique, and ever changing, to say one demographic has some explicit benefit to a business over others is short sighted. like @Andrew Johnson said, you want to evict grandma in December when the time comes?

I want to start quickbooks to help get organized (for LAST year 2017) and get it ready for my CPA.