Apologies for the delay in reply but there's a few things to unpack here and I wanted to give it some thought.
I'm reaching the big four-oh. I'm blessed in that most of my hobbies revolve around software development, which I also do professionally. That's not to say if I had "FU money", I'd keep my 9-5 (I very well might, but it's still a job). I've been pretty much full-time employed at a good job since I was 19--first in systems, then in software. Incidentally, I landed that first "real job"[0] by taking a pay-cut to $8.00/hr assembling PCs, installing networks and writing software for small businesses for a year to give my resume the appearance of more skill than I thought I had (turned out I was perfectly suited for the position but lacked the confidence to recognize it at the time).
> therefore not caring about lack of benefits from work and possibly being part of the no votes when my coworkers vote to unionize
I'll stay out of the union debate. Where I live, I've mostly watched the unions serve themselves and their leadership rather than the people in them, so my perspective is biased unfavorably. While I wouldn't join a union, personally, I understand why people choose to.
> general frustration with younger folks having many barriers to stability or opportunity by being crowded out politically and in the workforce by those who've had years more in better economic situations and just can't seem to develop a life that isn't revolving around consumerism and lacking in significant social/familial time investment
... and there's the biggie. I don't know what to tell you that won't come off as belittling -- not my goal at all. So I'll share with you advice that I turned to when I was making $8.00/hr eating Ramen noodles (and none-to-pleased with my current situation in life). A buddy of mine said "if all you want to do is make money, that's easy, read about arbitrage"[1].
I watched a guy get laid off from a $85/hr network tech job and when the two months severance ran out and the mortgage payment came due, he discovered that he could make his paycheck on garbage day if he drove his SUV through the right communities. That's all he's been doing for the past decade. He loves it because it takes 3-4 working days a week, a lot of the inventory is free (he buys things on Craigs/Offerup and sells on e-bay, occasionally, but often just grabs appliances that people leave at the curb). After discovering that about half of the things he picked up still worked, he invested in a box truck so that he could deliver the working ones, locally (which turned out to be a big deal). Heathcare was the big issue (I want to say he was paying $2,000-$3,000/month for terrible coverage for his family), but he sorted that out last year.
Having served at my church for a few years, I have hundreds of stories of people who hit bottoms like "homeless" and -- almost always through others (often strangers) -- found a way out. That's not meant to belittle those who are struggling or imply that their circumstances are their own fault. Frankly, it doesn't really matter who's fault it is--the person who has the highest probability of fixing the problem is the person experiencing it.
I was lucky (privileged, whatever), though, to be born to my Dad. He was one of 7 kids living in a 2-bedroom house (his "bedroom" was the couch and in his 70s, he's never lived alone or had "his own bed"), went right into construction work building garages, almost joined the construction union but decided to go into sales, instead. He was a good salesman but the commissions were weak. Despite that, he managed to somehow support a family of 4 well enough to save and buy into part of a company. We went on tons of trips -- they were all paid for via cereal box tops and by us tagging along on one of Dad's sales calls.
That company was later sold out from under him, he sued the owner and won but ended up paying more to the lawyers than his winnings, meanwhile he opened his own competing business and worked without a paycheck for two years so his staff would get paid. He's retired, now, and very comfortable but damn ... as his child ... I'd say watching what he went through was the single strongest vaccine against opening my own business he could have found.
The people I know who are "financially independent" (wealthy or otherwise, money isn't in the top 10 of their concerns) -- the first step was getting out of "hell", you can't get out of debt/become wealthy if you're searching for money for your next meal. Covering as much of that as possible and putting every remaining penny back into other things. Doing an 8-5 on a W2 is a reliable, consistent and predictable way to make money. Understanding that making money is a matter of convincing another human being to trade green pieces of paper for "something", and that acquiring said green pieces of paper doesn't have to be done by following your dream/doing what you love but can simply be "a means to having more money to do the thing I love with" or to ultimately getting to the dream job. Hell, my in-laws made most of their income two years ago selling elephant ears at fireworks shows[2]
I don't know your situation and -- as previously mentioned -- this is not meant as a judgement. You may find the only way you can get past those "barriers" is to move somewhere else for a bit. We joke that Ann Arbor, Michigan is basically missing almost everyone between the ages of 25 and 40. You can't afford to live there unless the bank (or school) is paying for school or you're already wealthy/retired from your U of M degree. You may be in a spot, like me, where moving is absolutely not an option.
Not sure if any of this was helpful but feel free to reach out via my profile and best of luck to you.
[0] At the time, graduating with a CS degree -- according to terrible, paper, sources provided by my High School -- would land between $35,000 and $45,000 where I live, so I considered any job that paid within that range to be a "real job". I'm not saying it's a good gauge, it's just the one I used.
[1] Not two years later this same person approached me for a $10,000 "investment" in a "pet rock"-like fad of these styro-foam balls with pictures on them that people attached to their antennas. The intelligent man in me turned him down without much consideration. I'd have about $70,000 had I trusted the guy.
[2] You wouldn't believe how many $7.00 elephant ears (that cost all of a nickle) you can sell in 3 hours, or how long it takes to get that smell out of every pore of your skin.