(non-native English speaker here)
I am thinking about starting to study Classical Japanese again. However, in the past I have always had a lot of difficulties in reading classical text, and later I realized it was because I am very ignorant about Heian-era culture and society, especially all the different ranks in Japanese courts and, more marginally, the role Buddhism played in people's lives. I am sure knowing more about these topics would help me immensely to read classical texts, since they are heavy on indirect allusions and similar stuff.
An ideal book would focus more on society and lives of people of Heian Japan, and less on historical events, but I don't want to neglect them, either. Do you have any recommendation for me?
You might be interested in the recommendations I gave on a previous thread asking for books about Heian court culture. The notes in The Pillow Book Penguin Classic edition are particularly good for explaining the court culture.