How come those that had a lot of help are so (judge-mental) hard on someone that had to go through it alone?

Because they feel that they did it all by their own hard work. And in many cases they, in a way, are justified. They just forget that the opportunity to work hard at something that pays off is simply not available to everyone.

I worked hard to get good exam results at school and to get my degree and at work. At each stage the hard work paid off. But what made it all possible was that I attended a very good primary school that prepared me well for junior and senior high schools that were similarly supportive of not only the obviously academic but also those who found school difficult.

And then uni. That was so much easier in the UK in the 1970s than now because the state regarded a university education as an investment and paid not only tuition fees but a maintenance grant so that I never had to work while at uni at anything other than my studies and ended with a degree from a good uni and no debts. Anyone my age in the UK who looks back on a successful career should consider how much of their success was due to free further education.