When traveling through several countries in a row, I always check the validity of my documents, and the page https://www.globelink.eu/already-travelling-travel-insurance.html can be useful for EU and EEA residents already on the road. For long-term travel, it's especially important to consider the total period of absence from your country of residence. I also check whether the selected geographic area covers each destination. Do you consider the total period of absence from your country of residence when choosing coverage?