Tools like the BiggerPockets calculator and books like The House Hacking Strategy can guide you further.

Think about the person booking, what are they looking for? 

Tony Robinson and Ashley Kehr have a BP book on Real Estate Partnerships.

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.2.

We also use Rental Guardian and add the charge to each booking so essentially the guest is paying for their own damage insurance.

My guess is they have low level of book keeping sophistication. 

Without writing a book, google these two terms.Zombie CondoHOA Special AssessmentThen search for news on condos in Florida from this year.

.- If you decide to have an LLC for each property, creating a Management LLC that all the other LLCs "hire" to run their books, will allow you to only require a bank accont for the Management LLC.2) You may not be able to do a Trust.

So prompt responses to inquiries generally get the bookings.  

The property will need to have a slight rehab to get it up to STR standards, but when complete it should easily be a $200k Gross booking revenue property.