Message in a bottle
There have been a tremendous number of articles on Sailnet related to just these topics. The category used to be called "Finaces Afloat" and covered everything from preparation, to expected costs, to insurance. Unfortunately, the new format at Sailnet makes it difficult to find these articles easily any more.
But, here are some suggestions to find them.
1. Some of the best articles have been written by "Sue and Larry". If you look through their listed articles you are likely to find these easily.
2. Search Sailnet for "Finances" and "Health Insurance" or just "Insurance".
You will see that taking on a cruising lifestyle may be a lot less expensive than you think.