Should you show sympathy when the loss could have been avoided?

While on leave recently I called into the Eumundi Markets and struck up conversation with one of the local artists. She asked what I did and then explained that after nearly 40 years of paying for motor insurance, her husband elected not to insure their car.
Within two weeks of the insurance expiring he was driving at 6am in the morning. It was raining very heavily and the only other car on the road at that time in the small community stopped in front of him and he ploughed into the back of the car in front.
Not only is he responsible for his own car, he is also now being chased by the insurer of the other car for the $4,000 + damage to that car.
It is just staggering the number of times this sort of story has been told to me. The perceived saving in premium made is suddenly exchanged for an unbudgeted expense that this family do not have the funds to cover. They have maxed out their credit cards to get their own car fixed as not having a car is simply not an option. They will get through but they are really doing it tough. I purchased a piece as my way to help them.
Only last week, two of my team meet with a client at the request of their broker. This client had decided that Business Interruption was not necessary for their business. This was against the advice of their broker and our claims team despite being explained all the risks of not having the coverage and the benefits of having it.
No matter what was said this client could not be swayed. The old adage that you can lead a horse to water but cannot make him drink is certainly true. Sometimes, as in this case you cannot even make them thirsty.
The question I struggle with is should I have sympathy for this type of client when they do have an insurable loss which is not insured despite getting good advice.
On the one hand, I cannot help think that you have no one to blame but themselves but despite making my own job in assisting a business survive a loss, I still feel sorry for them. I am starting to question whether I am fair to myself in taking on the worries of others when it was so easily avoided.
The only thing the broker and our team can do is to carefully document the discussions and the advice given so that neither the broker or our PI insurance becomes the last line of insurance for this client.