Yes,no,no,yes,yes.
I had to read Sense and Sensibility in HS...really did not 'get' it, or Dickens. I also read both Catcher and Mockingbird at that time or a bit later, and found them both far easier to grasp. Later I was reading Jane Eyre,some Dostoevsky, Hesse,Hardy,...even Dantes Inferno.
I got back into the classics after a 20 year lapse when I got an ereader last year. After doing some OU courses that focused on the Georgian/Victorian periods,all the classics of that period made so much more sense. I like being able to compare the life of a young woman as depicted by Austen with our modern world.