n0, I agree on most points you are mentioning. Some comments:
Lack of education in Pale: it was very attractive to get education. If you are a doctor or a merchant at certain level, you were even allowed to live in central cities. Whom do you think R Yitzele _Peterburger_ was a Rav of? (in truth, the only thing he liked there – streets are clean so it is possible to think Torah while walking there). At that time, education correlated heavily with conversion and assimilation.
Value of education now: it is well possible to go study gender studies and then appeal to the government to forgive the debt. As any tool, it has to be used correctly. A lot of professions ensure comfortable life-long middle class employment – engineering, software, accounting, office management, nursing, therapists, technicians … Are there dangers here? I think they are less than in previous generation.. We have Jewish colleges in NY and NJ, we have online degrees. Maybe we need consultants within the community who can guide students towards right approaches. Of course, lack of necessary skills at high school level may be a problem.
Businesses in the community: I am all for that. We do need more Jewish business interacting with each other. If our ethical/business values are strong, all Jews (and non-Jews) would love to sign up Jewish accountants with arbitration according to the local beit din. Trump said that, so some people see value… but when work opportunities in the community are limited, it is not healthy. A lot of people see chinuch as an only job venue. This seems to conform with halakha – make teachers numerous and poor but provide best value for teaching children. Except, the key halakhic instrument is missing – unrestricted competition between teachers. Instead, we mostly have schools that “sell” teachers as packages and partition the market between each other by hashkafos. So, we end up with (some) unworthy teachers who are not happy themselves and are not helpful to kids. Many of them would have been great accountants.
Earning a living – It is not problem to be poor and learn Torah whole day. I don’t know – is it popular? Make your shabbat like chol – and Rabbi Akiva knew what it means to be poor … How many people skip shalosh seudos in order not to rely on charity? I think being an erliche Yid (old fashion value, I know) precludes relying on taking money from others, whether Jews or state.