I wonder how many people pay into Medicare their entire working life and pass away before becoming eligible to use the program they paid into for their entire life? What happens to those funds? Does The Dearly Departed's Family get that money back? Are there enough people who pass to help level out the field money wise?

It's an insurance premium just like the car insurance premium that you never get back. It goes to pay for medical care for those who need it. But, sadly, it still is not enough to cover the cost of the benefits that are paid out. The system is broke because they are not charging enough to cover the benefits that they pay. No, it does not level out.