The cost of interest you are saving on such a small amount of money is probably negligible. 

Umbrella insurance which is an extension of your General Liability coverage will defend and cover any damages so long as the triggering event is not an exclusion in coverage (gross negligence (sometimes mere negligence), willful misconduct, fraud/misrepresentation, illegal use are common exclusions in property GL policies. 

There are now so many resources and so many people to answer those questions, that you are officially negligent if you don't speak up and take advantage. ;-)That's a start.

There are now so many resources and so many people to answer those questions, that you are officially negligent if you don't speak up and take advantage. ;-)That's a start.

That means they’re expected to exercise reasonable care and diligence in managing the property.So if the damage is extreme and clearly developed over time, the owner could argue negligence — that a reasonable manager should have noticed warning signs (maintenance requests, odors, excessive utility usage, etc.) and acted sooner.It might be time to review your agreement with that management company...

Agree, especially if you have been negligent you have no legal protection from the LLC.

With a true home run, it should be easy to go back to the bank for a revised loan amount to cover the roof replacement and should have negligible impact on the property's performance. 

Prosecutors sued the owner and leaseholder for “negligently ignoring safety hazards.”

If you look at the interest expenses on a flip with an interest rate at 6% vs. 10% just as an example, assuming the investor knows what they are doing and executes efficiently, the added interest charge really has a negligible impact on the overall profitability.

If the paper trail shows clear negligence that breached duty and caused the loss, consult a real estate attorney to assess recoverability and costs; if it’s gray or contract-driven, negotiate a settlement through the brokerage’s E&O carrier.