2- how much capital gains do I have to pay in Puerto Rico after living in PR but selling a property located in FL. 

A good professional can often pay for themselves by increasing your rent rates, reducing vacancies, or protecting you from bad renters.

You are far better off buying a stand-alone vacation rental and paying for a hotel room when you need it.  

You can pay a flood mitigation company to do this, but it will be expensive.

Pay cash, cash is king.

If so, I will obviously pay for it since it is my fault but I wanted to make sure first that they were not going overboard before I pay over $1,000 for it.

Should pay its self back within two years.

Are they still paying rent?

Why I Love Student HousingRent Premium - Students will typically pay 40-50% more in rental income than market rate housing.

For example, I mention that every adult must pay a $30 application fee, pass my credit/criminal background, make a combined income of 3x the rent, and whether or not the property accepts pets.