I think rich people also marvel at the failure of the middle-class to not go to the right schools, make the right connections, marry into the right families, not take "full advantage of the tax code" (e.g., for Americans - bank offshore).
Although you're probably not wealthy enough to go to the right schools, you may be able to get in via scholarships.
Although a middle class pool of good connections is limited, there are ways for a creative person to seek out better ones, often by something as simple as changing their environment.
Tax code knowledge is useful and valuable, and can be learned if you're willing to put the time and effort into it.
My point is, if you wish to elevate yourself, you must first study those whose ranks you wish to join. Learn how they acquire, and, more importantly, keep their wealth and power, and find ways to do so yourself, even if you have to be scrappy to do it. The whole startup thing does just that in the business world.
There will always be things you are simply blocked from doing. Instead of focusing on how unfair that is, focus on the things you CAN do, even if it requires greater effort or a more creative approach than someone more privileged would need.
This is aside from obvious cultural differences WRT the type of status symbols and such.
Are you saying rich people are better able to estimate the risks and trade-offs for their decisions?
I should point out I'm talking more about "people who become rich on their own" rather than lucky lotto winners or lucky selection of parent or trophy spouse or whatever.