How we cite our quotes: (Book.Chapter.Paragraph)
Quote #4
It became at once vivid to him that he had originally had, for a few days, an almost envious vision of the boy's romantic privilege. (2.2.9)
It's not easy for him to admit early in the book, but Strether realizes that he's completely envious of Chad's life in Paris. After all, Strether spends his life sitting at a desk and editing a magazine that his fiancée basically created just to give him something to do. That's not the best way to feel satisfied in life.
Quote #5
Chad had at any rate pulled his visitor up; he had even pulled up his admirable mother; he had absolutely, by a turn of the wrist and a jerk of the far-flung noose, pulled up, in a bunch, Woollett browsing in its pride. (4.1.41)
Strether's dissatisfaction with his life only deepens when he realizes that Chad's flashy new personality not only makes his own life seem pointless—it also makes all of Woollett seem boring, even Strether's moral hero, Mrs. Newsome. So all the stuff he did feel satisfied with starts making ye olde switcheroo.
Quote #6
His changed state, his lovely home, his beautiful things, his easy talk, his very appetite for Strether, insatiable and, when all was said, flattering—what were such marked matters all but the notes of his freedom? (4.2.3)
There's almost nothing in Chad's life that doesn't make Strether dissatisfied. The way he talks, all the cool stuff he owns, his zest for life. In short, Chad's living the good life, and Strether has been too blind to realize what that really means until it's too late for him. Strether's old now, with no hope of ever making the money or being young enough to live like Chad.