Any suggestions and recommendations are very welcomed and appreciated!  

@Zachary Harrison you have some great suggestions here from others.

Suggestions?  

Any opinions or suggestions are most appreciated.

Hi - congrats on purchase, Championsgate is a great STR area, as somebody who owns and manages homes in the area, I would suggest you use a STR broker, Fudge insurance are in Orlando and specialize in STR homeowner insurance, we use them for both our properties, but also other insurance needs.

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

Follow my original suggestions above.  

I was thinking of giving him 3 options.Option 1: He switches to a month to month lease changing to a weekly rent rather than monthly, the new lease will have different rules (ex. such as agreeing to a cleaning schedule and a liter schedule or trash needs to be picked up and placed in a trash can every 12 hours, human waste can not be stored in containers)Option 2: He moves out at the end of March, I keep the security deposit as rent and he does not have to pay February's rent and late fees.Option 3: I'll give him $400 to move out 3 days after we have this discussion.Thank you for any suggestions, I would like to handle this delicately as I don't want a squatter living with me.

I would suggest looking into private financing options.

I would suggest you hire an inspector as well as have a general contractor go out to the property.