In some places there are a few days grace period to allow for rent that is sent via mail (which I don't get because if it is due on the 1st, plan ahead). 

They may just vacate.

I am serving her a notice to vacate at the end of her lease in feb. 

Like @Collin Hays said, it is being driven more by neighbors tired of poor STR owners not keeping things sorted.We only look for places in vacation areas with a long history of owner driven STRs vs big cities and the like.

Since you only have 2 full time and two part time staff, who covers their vacations and sick time?   

Ordinarily those tenant vacated damages would be too remote, but it sounds like they were contemplated by both parties at the time of contract.Were I in this situation I would be looking to state law to determine if the EMD is truly the extent of my potential liability as a buyer. 

This translates to high rental demand and potential for appreciation.Diverse Opportunities: From bustling metropolises like Miami and Orlando to charming beach towns and vacation destinations, Florida caters to a wide range of investment strategies.

@Tonio PearceYes you should create a business plan.

As soon as one violation is discovered, send a Notice To Quit advising them to stop/cure within your state's time mandate (mine is 3 days) or vacate the property.  

So if the homeowner saves energy or goes on a long vacation, they still get charged 100%.