However, insurance is limited because it only protects you from one type of liability: accidents/negligence.

I have talked to attorneys and I know one that has lots of RE and he does not even have properties in LLC's, as he said you have to be severely negligent to get sued and lose.

For example, something terrible happens on this flip your considering and you are found negligent / liable… An LLC will provide for a cushion and offer some protection and in most cases, it will protect your personal assets (Not Always).

Talk to the repair person and if the damage is due to negligence by the tenant, then have them reimburse you for the costs.

Or you get a policy without an exception for a defect either because of negligence or a deliberate decision and then you either can't sell or refinance because another title company won't insure over it or worse, you find out when you're sued and wind up in litigation for several years. 

I would look at having the PM company pay for any additional fees/lost rents etc. as a result of their negligence in representing you. 

I have a bachelor military tenant, whom was negligent and never cleaned.

Anything that breaks from a tenant's direct vandalism or gross negligence is on them.

If they waited an unreasonable time before initiating those steps, or were otherwise negligent, they MAY be liable to some extent.

I don't know if there's any hope of that.It's not a gigantic amount of money but I feel that this title co. is generally incompetent and no doubt has already screwed someone else over through their negligence since this happened to me.