Money helps one economise on thinking just as it spares one from housework. The poor learn to distinguish the nuances of a good's quality and to analyse their own tastes so as to identify a bargain. By contrast, the rich exploit the association between higher prices and higher quality, and channel thus conserved mental exertion into more rewarding pursuits. The habit of relying on that association, however, can leave transactions insufficiently examined when prices are dominated by social conventions and status, which may be irrelevant for many. Holden Caulfield is benevolently neglected by his parents, who buy him expensive education without trying it on first and then overlook the inflicted blisters.
The importance of wealth in helping isolate oneself from disagreeable strangers must not be underestimated. The wealth of the Western world accounts for its peace, which prevails not only because wealth educates and raises the losses from conflicts, but also because wealth makes it easier to be tolerant---by having insulated oneself from the tolerable.
For Caulfield, however, family wealth is a poor point of departure. His wealth compels to conform, expands choices but does not inform of their consequences, suggests anarchy as the sole cure where a less wealthy would apply hard work. Ascending the social ladder confers the responsibilities that can be overlooked by those born at the top. Caulfield squanders money in order to descend to the position from which he would feel comfortable starting.
Intelligent, perceptive, and immature, Caulfield is a critic who has not yet become an artist, which would require kindness, in addition to his tolerance of bores and beauties. He lacks kindness to those who are kind to him---whatever their motivation: politeness, unrequited love, or the expectation of profit. He needs the society of multiple generations and social classes---not just his peers---in order to motivate his creativity. His character requires nurturing that is informed by more than just the prices of various boarding schools.
The adult Caulfield would think as the teenage Caulfield does, but more abstractly. The task of a successful civilization is not to break a rebel, but to accommodate him profitably.
It takes maturity to appreciate the division of individual efforts contributing to the civilization and to realise that often one can help more individuals in more substantial ways by acting indirectly, sometimes impersonally. Mr Antolini, Caulfield's teacher: "But I do say that educated and scholarly men, if they're brilliant and creative to begin with---which, unfortunately, is rarely the case---tend to leave infinitely more valuable records behind them than men do who are merely brilliant and creative. They tend to express themselves more clearly, and they usually have a passion for following their thoughts through to the end. And---most important---nine times out of ten they have more humility than the unscholarly thinker."