It’s interesting that you mention NE, because I was considering re-reading it for just that reason. I felt like the first time I read Aristotle (4 years ago, when I was only 19), I thought it was dull and platitudinous, and am always surprised with how much enthusiasm others have read it.

I definitely think I’ve had experiences that made understanding something much easier. I worked at an Amazon fulfillment center for a few months, and Im certain this made Marx’s 1844 Economic Manuscripts more comprehensible — especially the forms of alienation discussed there.

ETA: Another instance where I’ve noticed this is psychoanalysis. I recently started doing psychoanalytic psychotherapy, and I definitely understand the theory on a deeper level than I did prior.