While this thread is pointless as to OP. No matter how many times people who deal with issues such as this routinely, make it clear that the first three things to do are:
1. Go to the airport
2. Go to the airport AND
3. Go to the airport

she pushes back. If OP were the passenger, I would simply let it go. It's OP's money. But, OP is somewhere in the hospitality business and there is nothing worse than providing misleading advice.

In many instances, it may be that you are certain that you've missed the last flight, when it turns out that delays don't mean that. It's possible that a carrier would hold an aircraft if there were massive disruption (or it might not). These things don't always translate into instant status updates and you won't find out about them until you get to the airport and perhaps learn that there is a flight when you thought that there was not.

There are others who come to FT and search for advice, so it is worth the discussion even if OP doesn't care to listen.

At a broader level, travel insurance is always a good idea. But, there is no single product and there are products which cover things you may not care about, e.g. checked luggage when you travel with carry-on only, and comprehensive products with exclusions making it worthless.

What is available to you and at what cost is dependent on many factors, including your residence. But, reading the policy language matters. Forget the marketing hype. What matters are the words of the policy.