The generational divide lines are fairly artificial, but there is also some truth in it. As you point out, a lot of the things that shape a generation are external events. There is also a divide between early and late Boomers. Hillary Clinton is an early Boomer and the Obamas are late. While their political philosophy are pretty much the same, the events that shaped them are different.
The Boomers and early GenX grew up under the "red scare". We still had duck and cover drills in school. Even at 7 I knew it was ridiculous to try. Early Boomers went through the Civil Rights movement, the high profile assassinations of the 60s, they faced either going to an unpopular war, or seeing their classmates or siblings go.
My parents were of the generation that fought WW II (they were/are old enough to be my grandparents and often were mistaken for them when I was a kid). When people of that generation get together, they always asked "what did you do during the war?" For the early Boomers it's about what they did during Vietnam.
Whether someone remembers the Civil Rights movement or not has a lot of impact on your world view. I was born after in a city on the west coast. The idea that people weren't equal was an alien notion until I was a young adult and saw it happen in Bakersfield.
I also have some Boomer attitudes in part because my sister is a middle Boomer and my parents were the generation that spawned the Boomers. I also grew up in an empty nester neighborhood, so all the neighbors were around my parent's age and the only kids were adults still living at home.
For the early GenXers, we remember the Moon landings (one of my first memories of the world was Neil Armstong walking on the Moon), we also remember the end of the Vietnam War when most people felt it was a bad idea. I have memories of watching the war on TV at dinner as a small child (with Walter Cronkite). We also went through Watergate. I remember watching Nixon's resignation live. Then there was the oil crisis.
All these things happened before the late GenXers were born. The early Xers were also suspicious of politicians after Watergate and Vietnam, but many were bamboozled by Reagan.
GenX was the first US generation since those born immediately after the Civil War who didn't face the prospect of getting drafted and sent off to war. That had an effect too. But it came earlier in Canada. I went to a convention in British Columbia when I was in my 20s and the bulk of the attendees were Boomers or those born during WW II. There were about 1/2 Americans and 1/2 Canadians. The American men (except me) were talking about what they did during Vietnam and a Canadian the same age commented that was a different experience Canadians of the same generation had. The Boomer Canadians had never faced the Vietnam question men of the US had to face.
One dividing line I've seen people make is the point you make about the Oregon Trail Generation. It is a different dividing line than standard generational mapping. For those born before 1955, it's unlikely they never encountered a programmable device until they were adults. For those born from 1955 to about the mid-70s, most encountered some kind of programmable device before adulthood, but they were occasional things rather than staples of the environment. For those born after the mid-70s, they grew up surrounded by electronic devices and don't really know how to live without them.
It's not universal, but I have noticed that those born before 1955 struggle a lot more with basic computer concepts (unless they were early programmers or something) and are much more likely to see computing devices as magic boxes they can learn to operate, but will never understand. Those born between 1955 and around 1975 are much more likely to get basic computing concepts and can figure out how a computing device works. There was that joke when I was a kid that if you want to program your VCR, find a kid. It was true in my household. I was the only one who could program the first couple of VCRs my parents had.
For those born after 1975, computing devices are just extensions of themselves. Doing things with computers are just natural and not thought out at all.
The early Xers had a quiet impact on the computing industry. There were quite a few of us who went into tech. It was one of the best paying professions in the 80s when I was in college. As a brag to others somebody in the School of Engineering had pencils made up at graduation one year saying "we have jobs!" Most engineering graduates had multiple job offers.
But few early Xers got rich in the tech biz. I was looking at people born in a few years on Wikipedia the other day and it was notable that Steve Jobs, Bill Gates, and one of the principle founders of Sun Microsystems were all born in 1955. I couldn't find any notable tech people born around the mid-60s. There are quite a few late Xers who were in the middle of the dot com boom and after.
At the time I didn't, but by the 90s there were some sociological work coming out on how the Reagan revolution affected GenX. For the early Xers, there were a lot of scares in the 70s and nobody seemed to know what to do and Reagan came along as the cowboy to save us all on the white horse. I never bought it, but a lot of early Xers did.
California was the first state to start getting rid of leaded gas. As the first unleaded gas became available, there were a lot of older cars burning unleaded without catalytic converters. I do wonder what those fumes did for the health of those exposed. The smell always made me gag, so I would hold my breath around cars spewing smelly exhaust. I still do around cold ICE cars.
In Los Angeles my childhood was the era of bad air. They had to yank my tonsils when I was 7 because they were so swollen I couldn't breathe. The doctor told my mother I had a very high risk of developing asthma, but it was that or strangling in my sleep. I didn't develop asthma as a child because the allergies to smog moved to my sinuses and I spent the rest of my childhood with constant sinus problems. They are scarred from the constant allergies.
When I moved away from Los Angeles at 18, my allergies went away and I experienced being able to breathe through both nostrils at once for the first time in my life. Once the sinus allergies cleared up, I started developing some mild asthma which still affects me sometimes today.
I was reminded of what it was like as a kid a few months ago when I had an allergy attack on par with a childhood one (first time in 40 years). I think I breathed in some burning plastic. I'm not 100% sure what it was, but it smelled like burning plastic.
Growing up with almost constantly orange skies, I've felt it was time we started phasing out fossil fuels.
Both early and late GenX are suspicious of what they're told, but the take aways are different. The early Xers came of age during the early days of the 6th Party System in the US when the ideas of the 5th Party System (New Deal) that had been gospel for 50 years were dying. Our early world experiences were in the miasma at the end of the 5th Party when the old system was falling apart and the new hadn't really come along yet. Then Reagan came along with new ideas that seemed to work and the early Xers were sold.
We're at the end of the 6th Party System now and the 7th will start as soon as a voice comes out of the wilderness to coalesce a new meme. The popularity of Bernie and Ocasio-Cortez tells me the new meme will be something along the lines of what they are talking about, but the right mouthpiece to make it all gel hasn't come forward yet.
The impact of Calvanist Christianity is a big thing in American politics. Calvanism largely died out in Europe, but many groups just moved to the US. The more "liberal" Christian faiths like modern Catholicism, Episcopalian/Church of England, etc. either actively encourage or at least don't discourage free thought. But Calvanism has always discouraged independent thought and asking too many questions. Southern culture in general has also reinforced that thinking.
The right has learned a lot of lessons from 1984 and know media is a very powerful weapon for shaping thought. Keeping broadband out of rural communities allows them to shape thought in those areas through their mediums of Sinclair, Clear Channel, etc.
This country and many countries have split into two different worlds which consume very different media for the information that shapes their thoughts.
The myth that the right tells about how illegal immigrants are a burden on society is a massive untruth.
How undocumented immigrants pay taxes, explained
A lot of them have fake IDs to get jobs because the feds require employers to vet everyone for legal status and penalizes employers who knowingly employ illegals. A lot of employers who employ illegals do so with a wink and a nod, but want enough of a fig leaf they can claim they did something to vet the employee before hiring. So they have fake SSNs and other IDs they use to get work. Employers withhold from paychecks for Social Security, Medicare, federal income taxes, and local taxes. All those are sent into the government agencies. When the illegals reach retirement age, most will not claim those benefits.
If illegals are unemployed, very few are claiming unemployment or welfare benefits, they are just suffering in silence in the shadows, or leaving the country. These are people who want as little exposure as possible.
Because almost all illegals are poor, they spend most of their income. It was common for many seasonal workers to send money home or take it home when their work season ended (often farm labor), but they had to spend something while here in the US. As they spend money, they pay transnational taxes like sales tax, gas tax, and alcohol tax. All that goes into the coffers as tax paid.
They also pay taxes indirectly. Most have to rent someplace to live and the landlord pays property taxes on the property which goes into local coffers.
The tax footprint of an illegal is very similar to that of a native born American making about the same income, but the native born American is more likely to be claiming benefits like food stamps or Medicaid.
The claim that illegals are a net drag on our economy is as big a myth as trickle down economics being a good thing for all. We've been told the lie so often, most people accept it as the truth without thinking about it.
The three women who do Mueller She Wrote also do stand up comedy. The podcast is often interesting.