I have no idea how high value packages are shipped? Wrong again @wesheadley
I'm an executive at a medical device company. We ship large, very expensive devices across the US and around the world every day.
Things get lost, damaged during shipping, scheduled pick ups for RMAs don't happen, and getting paid on an insurance claim is nearly impossible and requires a ridiculous amount of time and resources.
Buying insurance often just means they'll look harder for your missing package.
You were lucky with your one experience with a UPS claim.
I also have one personal experience with a UPS claim for damage in transit, and they refused to pay it even with extensive photo documentation.