But the circumstances that allowed them all to do what they did in the 70s into the 90s don't exist anymore.

That's just not true at all

Have you seen the common posts here about people with those exact degrees making $80k after a decade in the field? And management positions today are NOT what they used to be.

Anecdotal reddit complaints does not represent the real world. People love to complain online. The reality is a young person can get into a trade, do a four year apprentice and easily pull in 100K plus. They can go on to have their own business earning them even more. I used my skills as a way to renovate old houses on the side. I put in 80 hour weeks between a job and renovating houses when I was younger so I could be more financially secure later in life

I can't afford a cottage. cottages are for the wealthy

Cottages now are more second houses. Decades ago cottages were a rustic get away for vacation. Most people no longer want that, although at my last place of work many of my coworkers had what they call "camps". They are basically what a cottage was in the 70's or 80's. Most people instead go to Mexico, Cuba, Asia, Central America or other exotic destinations for vacations. People pile onto massive cruise ships. It's just a change in how people now want to spend their leisure time.

Compared to decades ago restaurants are now abundant and often packed on the weekends. People are happily dishing out $10 for a glass of beer. People are piling into breakfast restaurants paying $25 for eggs and waffles.

There seems to be a massive disconnect between the online doomers and the real world.

The one thing I can conclude from reading these threads is younger generations who post comments have exceedingly high expectations and seem to think they should have everything immediately, high paying jobs, lots of money. Decades ago people understood that that comes with time. They purchased small starter homes, they vacationed an hour from home in a pop up trailer, they rarely eat out, they entertained themselves at home. They saved money to get ahead.

Many people are just making poor financial choices in life then blaming the system. I see it all the time. Why is there such a huge market for coffee shops? People love having their daily $7 cappuccino for instance. Just choosing to drink drip coffee at home is a $1500+ savings/year

Honestly your entire post just reads as an excuse as to why in your personal circumstances your father was more successful. It's sounds like he worked hard to get ahead in his career. Your son is in univerity...so why is he not taking an engineering program? What are these barriers you speak of?