I just had a lady move into one of my rentals who claimed she would be there for 2-3 years.

Mario,Discuss with the agents the specifics on the property (ie age of roofs and systems, claim info, pets, pool, etc.) before making any changes. 

Did they file a claim?

I know one investor who will literally record his discussion with his contractors walking through the contract, so that if they ever end up in court, the contractor can't claim he didn't know what the agreement was.- In terms of, "How do you manage contractors so you get the price you need, the quality you desire and the timeline you agreed to?" 

The guest claims the lock on the door wasn't secure enough or that they yelled for help but no one came out.

The biggest problem is speed of service on claims.

If you can prove the lender originated a loan with you and did not have the capital to fund the loan in its entirety, this might be a claim as you are going to experience delays, higher carrying costs etc.

I have a few rentals and my insurance is all coming due soon and everything went up without a claim ever on anything. 

We had a fire/landlord policy with Norfolk and Dedham insurance, however after my last tenant and last property manager allowed my property to get into a state of severe disrepair, including water damage from a dishwasher/septic backup, which was never remediated, my insurer dropped me from coverage as a "bad risk" (we had made a claim for the water damage by the tenant).

The Florida safe harbor seems to be a giveaway to the banks, since a regular purchaser must cover all outstanding dues, but the bank can claim the safe harbor benefit.