Many of James idiosyncracies of writing can be understood in terms of his character and background.
He was afflicted with a mild stutter. He overcame this by cultivating the habit of speaking very, very slowly and deliberately. This gave him plenty of time to think about things he might like to add or revise while still in mid-sentence and he did so with abandon. This carried over into his writing (he felt that good writing should resemble the conversation of an intelligent man), but his prose is at times baroque. (His friend Edith Wharton, who admired him greatly, admitted that there were some passages in his works which were almost incomprehensible.) His short fiction tends to be more readable than the novels.
For much of his life, he was an expatriate, an outsider, living in Europe (much of Portrait of a Lady was written while he lived in Venice-- a city whose beauty he found distracting). This feeling of being an American in Europe, came through as a recurring theme in his books contrasting American innocence (or a lack of sophistication) with European sophistication (or decadence). (See Portrait of a Lady or, perhaps, The Golden Bowl).
He made only a modest living from his books, yet was often the houseguest of the wealthy, not really one of them, but able to observe them at close range. (He said he got some of his best story ideas from dinner table gossip.) He was a male homosexual whose tastes and interests were rather feminine, yet as a male could travel and act with an independence denied the women of his time. Being a permanent outsider in so many ways may have helped him in his detailed psychological analysis of situations -- one of the strongest features of his writing -- because he was never a full member of any camp. (See The Bostonians, especially Verena's speech about always looking at the world from behind a sheet of glass.)
This analytical strain is his work is quite strong. It is possible to see many of his stories as psychological thought experiments. Portrait of a Lady might be an experiment to see what happens when an idealistic young woman suddenly becomes very rich. The novella The Turn of the Screw is a ghost story that deals with the psychological impact on an unmarried (and possibly sexually repressed) young governess who stumbles into an ongoing tragic love affair complicated by the fact that the lovers are, well, dead. The late novel The Wings of the Dove deals with the question of how far a woman in love will go to get what she wants and what it costs her when she does.
A good place to start reading is:
The Portable Henry James, edited by Morton Zabel
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