We're not the most regulated market, when compared to your San Francisos, New Yorks, etc. 

More so in a regulated space.

I called my homeowners insurance and the municipality to see if either entity would have an objection, but both said that as long as I don't separate the home into two units, they don't regulate occupancy per sq. ft.A friend suggested that if I allow it, that I should increase the rent substantially to account for the potential repairs and replacements that might need to be made. 

Anyone know how to contact someone at or associated with or regulator of RealtyShares?

In addition, I'd be appealing to any insurance company and the state agency who regulates the insurance company to see if they are responsible to pay even a small portion of the damage that may have been caused by something that was covered, like fire or wind & hail, etc., not just flooding.    

Wholesalers IMO can be sleezy, no regulation, no one to report to, it's kind of like the wild west.... one called and offered me a house -- $5K more than he posted it on the market.   

His son has been arrested numerous times since my run in with him so daddy might have raised him a bit wrong...

Are there specific rules regulating whether lease options can happen in Jacksonville? 

(You don't know what you don't know, as the saying goes.)The entire purpose of laws, licensing and regulation is to provide frame work to protect consumers.

There are numerous forums on this site to answer almost any question you may have.