I wouldn't only trust the word of the county person you talked to (they're not always correct unfortunately) but also supplement what they told you by looking at the published zoning code specific to the zone the property sits in (if you haven't already), and internalize the constraints as they relate to this parcel/your plan. 

My original goal six years ago was to supplement my W2 earned income, and then to replace my W2 earned income, now it is to 10X that!!!!

If you have not been supplementing with D-3 (your multi is too low, only 4-800 IU) previously take 50,000 IU a day for 5 days.

Is it possible that this also includes a supplemental bill for this year only?

They’re questions of supplemental income and do not go against fair housing laws.

I haven't taken it off of Airbnb yet and don't have plans to but I do plan to speak with a lawyer and draw up a separate supplemental contract as my Airbnb is growing rapidly and I feel like the extra level of protection couldn't hurt. 

I operate a business and expect consistent on time payments not nickel and dime incomes supplements through late fees.

If you are looking to truly supplement your income, you are going to need to significantly raise your unit count.

It is time to evict her.And for those who think this is cruel, I'm one of those "elderly" folks (I'm about to turn 65 in a couple of months and if I get one more notice in the mail about Medicare supplemental insurance I'll scream) and a breast cancer "survivor".Your tenant does have a daughter so she is certainly not alone in the world.  

Supplementing any tenants rent is a losing proposition that hobby landlords mistakenly believe is a benefit in retaining tenants but in fact has zero relationship to how long a tenant will stay.