Many elderly people are sensitive about a family member "looking over their shoulder" to check up on medical bills and payments. They may become defensive and take it as an indicator that you are suggesting they are not managing finances effectively. The truth of the matter is that navigating the health care system has become so complicated that many of us need professional help to make sure bills are correct and insurance claims are paid.
One way to approach a conversation about paying for medical costs would be to say something about how complicated everything has become – you could cite an article you have read or mention a story about a friend's situation to make sure your loved one understands that everyone has difficulty with this (not just them). You could even provide some objective evidence. For instance, according to the American Medical Association (AMA), one in five medical claims is processed incorrectly – so it's a very good idea to check everything closely. When it comes to actually reviewing the bills and claims, it may be easier on your relationship if you hire an unbiased third-party (i.e., a billing advocate) to do this task, just like someone might get professional help with their taxes.
A billing advocate may also be able to find other ways to save money by reviewing your loved one's insurance plan and usage to see if there's a better plan available. Relying on a professional can save you valuable time and energy with the added benefit of avoiding having to add this difficult conversation to your family dynamic.