As soon as housekeeping gives the green light I reach out, thank them for being great guests and offer 15% off a future booking if they make it within 2 weeks.

This way you can utilize the leverage if you plan to scale up in the future.

Stay tuned and work with their folks for details, should be some exiting things in the future.  

If in the future they try to buy a house, the lender may require it to be paid but that's a long shot. 

Plus, they provide great opportunities for cash flow, especially if you’re looking to scale and reinvest profits into future properties.If you’d like to connect or chat more about strategies, deals, or even market insights, feel free to reach out.

I would say go for it if that is what you expect to incur in the future or you are still growing.

Below is a link to the rent assistance program in Canton, Ohio; I would collect the current rent from the family and then provide them with this resource for help with future payments. 

Even if I am to not be taking home the lion's share of initial deals, I'd like to still be building some capital for future dealings.

., not available for rent) cannot be deducted as current expenses but must be capitalized, adding them to the property's basis for future depreciation once it's placed in service.

Once you trim it down to the better properties you can be pickier on deals in the future.