R214 I'm a first-generation college student who had no college savings, and I chose to go to a community college and then transfer to a public state university because of cost rather than opting for GWU, AU or maybe Georgetown, which were insanely expensive to me.
I have worked with community colleges for about 15 years, and of course I've lived through our country's growing wealth divide.
I've noticed a couple of things related to your post.
One is that people who have what is now simply called 'privilege' (I dislike the use of this word in this way because I grew up hearing of privilege with positive connotations.) are generally oblivious to real-world hardships faced by others. Here on DL and elsewhere among Democrats, a lot of people assume that this is a Republican-/conservative-specific phenomenon but it absolutely is not.
People who have been given or who have had easy access to/no life-related barriers (health, etc.) to cruising along evenly in life generally do not grasp the reality of hardships.
Most people are self-referential, and if they did it, then you can do it, and if you don't do it, then you are just lazy or stupid.
Most people do not realize that even though they worked hard to get what they have, X, Y and Z hardships did not apply to them and so, yes, they have had an easier life than some others and most people who are not 'at their level' are not lazy idiots; they are people whose lives have been challenging.
So there is that overall.
The harder thing for many of us to grasp is that even when we understand and accept it, we still act according to this for the most part. If your first inclination is "no, I don't," you likely still do.
Here in DC, there's a species of ultra-"privileged" people who I call Bethesda Liberals. They are very far left philosophically, they lead government agencies, news organizations, nonprofits and medical practices, and their hearts are charitable and caring. They feel at one with the common family and they want to help. Always from a patronizing perspective, though. They look down from on high and want to help and they believe they believe all people are equal except they certainly are superior. And I have learned that one shallow layer beneath that, they do judge people who are in their views less accomplished and believe in this idea of a meritocracy and think everyone is equal and therefore the really good ones are the ones like them—charitable, highly educated, rich people in neighborhoods like Bethesda and McLean and Potomac.
There is a real blind spot that I think everyone develops among people as they gain whatever kind of status and they become, even when sympathetic or piteous, unempathetic, unable to relate. We apply our own life's circumstances to everyone else's, and we empathize when we have experienced similar harships and do not empathize when someone has faced an unfamiliar one, even if we feel sympathy.
I have learned this with my health. I had a real health crisis throughout my 30s. I realized while going through it that I never registered how challenged just getting along in life and keeping a job can be when one is seriously ill, and how variable symapthy is. If someone has breast cancer, the world has been trained to lavish them with sympathy (if not actual help). If one has a rare illness, people question whether it is real and show only superficial sympathy with a weird passive aggressive resentment that is acutely felt.
Given that we're mostly self-referential and selfish, capitalism is a set up for "privileged" people to ascend smoothly and only look down on those who are trampled. They cannot relate. Nothing can make them relate except losing it all.