I would check your local legislation to see if holdover rates are capped.

The legislation and the courts are set up to be enablers of these miscreants.

Check this out and scroll down to the heading "States ranked by best legislation for renters:" Vermont, anyone?  

New legislation introduced in the House and Senate seems unconstitutional to me.

A short term rental unit is only a few bad reviews from being ruined and one bad piece of legislation being passed by the local government banning them. 

Read up on all the legislative issues and insurance issues with condos in Florida. 

While a great tool (especially the prior legislation version), I frequently see properties trade higher than they should because buyers analyze the properties with an extremely narrow lens without appreciating the favorable impact the abatement has on operating expenses.

So part of your due diligence before such a purchase has to involve trying to determine if legislation will be passed that prohibits short term rentals in the locale of your purchase. 

Some of our ocean cities and then sub-cities surrounding the capital Providence is beginning to try and restrict the amount of STRs, the geographic locations they can be in, setting up legislation that requires specific permitting use, and so on. 

My properties are in Oregon and the state is legislating several laws that are very landlord-unfriendly.