Gross negligence often comes in the form of folks just not understanding fully their policy and most are not going to hire a lawyer to read over the insurance policy hence we like doing the additional asset protection.

I'd recommend that you weigh the potential benefits against the additional workload and potential difficulties that comes along your way.

I am a newer investor (currently 1 short-term rental in addition to my primary residence) looking to purchase a property that I will make into a short-term rental. 

We acquire additional liability insurance and third property manager where we have an attorney review the indemnification clause.

Positioned on a corner lot, it boasts covered off-street parking with additional guest parking on the side.

Additionally, the charming architecture of the homes along the street enhances its appeal, making it a prime destination for investment.

Ask them to please be more mindful and if it happens again, add it to their ledger per their lease.

This won't be a flip, but to rent out to section 8, but I'd like to get a chunk of change via cash-out refi so I can acquire another property. 

It will be cheaper and easier to pay them and avoid additional fees or interest.Disputing the charges is the best step. 

If it is a covered loss, the judgement would need to exceed the limits before anyone would want to go to the additional litigation to try to break through the trusts.