The fact you’re writing this shows great dedication and curiosity. I’m not arguing with you, but I’d like to suggest another approach.
I’m a retired college lit teacher. I’m afraid that some teachers (high school and college) assume that every great book has only one point and that teachers are the curators of that point (which they got from their teachers etc.). So I’m interpreting your title as saying that you often don’t get the point that you think a literature teacher would say you should get. In reality, three lit teachers will have (at least) three interpretations of a classic, so when a teacher tells you there is only one point of a book, she/he is talking about classroom politics not the interpretation of literature.
I agree that a two-page prep would help before reading a classic, but all you need is what you’re calling “context.” Most theatergoers in Shakespeare’s time were not college-educated, but they would have appreciated his plays without any kind of preparation, because they already had all the knowledge about politics and language of the time that they needed. A hundred years from now, someone reading Cujo will need a two page prep in order to appreciate the book fully. Someone who watches the latest Star Wars episode without knowledge of the rest of the series won’t get much meaning from the movie.
Once you know the background, you will absorb the meaning of the symbolism and theme subconsciously. If writers wanted you to get a particular meaning from their work, they would have written a book of philosophy, not a work of fiction, or they would have included an answer key with the meanings of the various symbols. The more you read, the more you learn to pick up on symbolism and theme without having to think about it.
My recommendation: Read as much about the background of the work as possible before beginning. (Before you start Dante’s Inferno, for example, you should know what people in the Middle Ages thought were the 7 deadly sins and why they were considered sins.) But if you see an article or book telling you what the meaning of a particular classic is, skip it (you may want to see their interpretation AFTER you’ve finished the work, in order to expand your viewpoint, not to substitute theirs for yours).
Besides a bit of background, all you need to appreciate a classic is the attitude “I’m going to do my best to enjoy reading this.” If you’re not excited by what you read, put the book away for a while, maybe look at a little more background, and come back later.
Literature is the long way through the truth. It’s the scenic route. Enjoy yourself.
