You can also write off travel to and from the property and more.

There are definitely pros and cons to all situations, you would just need decide what is best for you.Would listing it as a mid-term (traveling nurses, doctors, business professionals, contractors, etc) or a short term rental be an option? 

I am open to both the Gulf side or Atlantic/east side of south Florida.I plan to travel to FL early next month and want to have some idea of good cities/regions to start with.

I've been in Lisbon for around 4 years - initially travelling between London and Lisbon before settling.  

I have lived in both places but if comparing price and travel time I don't know which one to decide on.

I will be traveling across the US to a better housing market, I have access to the MLS for every state which is cheaper than hiring a realtor and will make my journey better and faster.Also I have no income I live on disability and invest that into stocks, I worked a few months in IT and saved everything and quit so I could buy time.

Are they an executive, an employee on 6-month business travel, etc.?

Sounds like a cool idea though...the only place I've seen them is outside the US on Travel channels and such.

Are there public right of ways that are your responsibility and frequently traveled by guests or passersby?

I have had travel nurses, medical students, and military members stay for multiple months in some of my STRs.