Dress properly. 

Did a past landlord have damages that are documented in a court case? 

The current landlord does not have a check in/checkout list so the damage caused is not officially documented in writing so far, only verbally.

Do I need to actually pay my tenant every year, or do I just include the accrued interest with the security deposit (minus any expenses for damages) at the time the tenant moves out?  

Am I justified in using his security deposit to repair the damages?

Yes it was bad in certain areas (closer water and flood zone) but the rest of the population had more wind damage more than anything else.

If you provide anything in addition to the property being leased, and they can argue your negligence damaged their property (i.e. leaving an old refrigerator in the unit), they can make a compelling case that you're in the wrong when eviction time comes around.

If someone slips and falls on it tomorrow are you liable for damages?

I can tell you that lawsuits have resulted from discrepancies lesser than 300 sqft resulting in monetary damages.

Gives you some good tips on how to bullet proof your house to protect from tenant damage, inspections, etc... some basic information.As a cautious investor be sure to study the section 8 strategy very carefully.