@Juliet Silver fellow local here to Miami.

If it gets rented the owner will update the listing with a new available date; if this moves by 30 days or more you can reasonably assume it was rented.

But, then when they ask me the rent, the terms, available date......

Block out the dates of future bookings. 

This might give a one-time (non-scalable) boost to cash flow, offer multiple value-add options, and allow the house-hacker peace of mind, via the assumed mortgage, in long-term breakeven or positive cash flow in the event that the value-add plans end up not being executed, and/or the person has to move out, and rent by the room or STR become unavailable for some reason at a future date.

These I have found are real, striving parents, working their butts off to provide the best housing and school system for their children.My ethos in this approach is exactly why we at LaPlante refer to them as Residents, as we consider "Tenant and Landlord" to be dated terms and rife with negative emotion.

Educate the land owner on the potential profit run the numbers and go over the basic proxy and blue prints.Make sure you have a seasoned and qualified Builder/GC because they can be a deal killer with wasted time and inflated material and extended completion dates.

As @Jonathan Greene mentioned this is kind of a dated strategy in the new price/interest rate environment.

Secondly, Rad diversified freeze for 6 months and don’t even give the exact date to pay.

Your tenants can set up automatic drafts for their rent payments, but make sure they do not set them up for the due date, as they will not process.