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

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.

Milwaukee has not been easy to BRRRR for the last 3 years: with ultra low inventory sellers just did not have a need to give a discount for condition.

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. 

It is no different than a loan company requiring insurance on your house or car.As @Dawn Brenengen said, require that they put you down as additional insured.

Thank you for the replies.What type of additional services can one expect?

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.

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