We plan to sell the units to 2 different owner occupants.

Adding a simple clause to your Lease Agreement similar to the following may save you a ton: Tenant is liable for any damage caused by the occupants of the property including, plumbing, electrical, and acts of vandalism.

So here are my lessons learned: 1) Ensure to compare your rents for the vacation rental at the occupancy rates suggested by @Evan R. or less.

It keeps the property looking in tip-top shape, the landscaper can keep eyes on the property more frequently than you can, and they can bring in extra help when there's an issue with the fence, sprinkler, fallen tree, etc.I want my properties to look better than owner-occupants' yards.

https://www.biggerpockets.com/member-blogs/10042You should be able to leverage the booking sites (Homeaway, VRBO, Airbnb) to get decent metrics and you can check out Airdna.co to see high level occupancy and daily rates for general areas you are looking at for free.  

(This would obviously be the best case scenario) I heard possibly using the number of occupants allowed that this might be possible?

I hate to be the bearer of bad news, but if you are living in it and paying property management the rest of the year, you will not cash flow. 20-25% property management for STRs quickly eat into most cash flow when buying in todays FL market.the STR market is saturated and continues to get worse. in turn you have less occupancy and less income. in the next year or so, we will evaluate if the STR market is viable anymore where we are at. 

Occupancy rate is not as important to me as gross/net revenue.

Her kids are now out of high school, so location is not as important as it was when she first started renting from me.But when she leaves I will have had at LEAST 3.5 years of 100% occupancy, 100% on time rent.  

They only want owner occupants.