Dear Always,
Your theories just are not true. First, there is an ancient concept called the dowry. Very traditional communities are still over the top with that. It has nothing to do with learning, working, or being insulated. That is the original source of what is going on. In the post war era, learning boys usually got a smaller dowry than working boys.
Now a short list.
1) The Pale was short on resources and opportunities. Lack of education for the available jobs, was not the issue.
2)A decent job is more about opportunities. Many educated people never work in the field they studied. And, almost all entry level jobs, offer training.
3)Most small business owners (In the yeshiva community.) had no extra education. They figured out their business on their own.
4)One of the big factors why young families struggle, is student debt.
5)The yeshiva community creates way more opportunities than secular ones. Because it is insular, it creates the need for many of it’s own services.
6)The major chessed organizations, create many jobs while filling cracks that society at large can not address.
7)Keeping apart from society did very little to prevent European assimilation. It was mostly where the locals were drunks who beat their wives and kids, that the keys remained separate. All it took was for the locals to be enlightened, and the Jews slowly (Or not slowly.) followed.
8)Back when America was a melting pot of immigrants, the Jews in America had absolutely on insulation. They struggled to maintain private Jewish schools. Sheesh.
9)The closed communities that lost basic Jewish values in order to survive, were hundreds of years ago. They closed their communities, so they should not get massacred.
10)Earning a livelihood, is not a basic Jewish value. It is a basic goal of human civilization.
Sorry- it’s a long list.