Sometimes you just have to realize that the best answer is often the simplest and over complicating things can just make it more messy.
We were kind struggling with how to organize our database from a person and organization standpoint in certain instances.
Organization : property management company
Person: property manager
Deal: property service sold - custom deal details fields: site name, site address.
Then we have the situation with board member at the property but not associated with the property management company that we do not want as contacts associated with the property management company.
Separate organization: 'Property Name Board'
People: property related board members.
All deals are associated with the property management company.