I'll make this as concise as possible.

Family member has a store.
Store gets broken into.
Front Glass is broken, some items were stolen as well.

Store is rented through a sublease.
Sublandlord calls glass company overnight.
Glass company boards up glass while we were present.

Glass company owner ALMOST goes ahead and orders glass.

We send a written warning (email) stating that we don't authorize this and if this repair goes forward it will either be done for free or at the mercy of the insurance company.

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On the insurance side of things - the broker has no idea what's going on. Sends out his own glass company for a quote.

Broker keeps asking whether payments have been made.

Broker is rude and acts in an evasive manner.

We escalate and complain. His manager send us emails with documents showing the insurance company had sent multiple emails to him warning of closing the policy if it's not renewed. Broker failed to forward these emails to the business owner. We are waiting for a final statement from the insurance company. The issue is the duration of the lapse.

Fast forward 2 months. We repair the glass out of pocket while waiting for an answer from the insurance but we don't pay the first contractor because he charged us MORE for drilling a few $20 pieces of plywood than the other company charged for installing a new large thermal glass (labour and material)

Obviously the easiest way is getting insurance to pay him.

The other option is small claims court?

Your opinions are greatly appreciated.

This guy is a vulture that wants my elderly mom to make payments on his Mercedes Benz.

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If you are not gonna contribute please don't leave rude comments. Last time (a different account and a different situation) I had a bunch of people tell me your mom should learn how to read contracts and it's our fault yet, with the help of some Redditors, I won against a big company and got a big refund.