I came from a similar background to what you're describing. My generation is likely the first to vote Blue instead straight-ticket Red. For me, it was a 1-2-3 punch of life events that deflated the core of Conservatism.
Living in LA circa 2006 turned me leaning-Republican, but that was because their "Liberal" image is mostly bullshit. If you actually watch how the sausage is made, it's every bit as Conservative as Wall St. Sure, Actors and Writers tend to the liberal side. But producers? Agents? Hell no. These guys would make Ayn Rand proud.
But they vote Democratic and push the actors and writers into the light, because they know their livelihood depends on not alienating any big group of people.
Don't want dox myself, but I have firsthand knowledge that the Producer's Guild was lying to the Writer's Guild when they said there was no money from online sources.
After some other ethical ugliness, I moved to the Deep South to be near family. Living here flipped me lean-Democrat. If you don't have a car to get to your insanely too-far-away job, guess what? You're getting a new job. No real transit to speak of. A lot of the people I met while living there intentionally hurt themselves to get on disability. It was a destitute, economically-depressed hell compared to what I was used to, even in the ghettos of LA.
In other words, I began to see the value of public investment. "If they just paid for a few routes, this place would do MUCH better. Who in charge is failing to look at cost-benefit?!" That was when I realized the idea of government "butting out" of things like public transit only created a dearth of opportunity, with only ideology as justification.
Finally, I moved back closer to home. Northern Midwest. I still clung to the idea, in early 2008, that even despite all the new things my experience had taught me, I was still personally responsible for my own success or failures. And those individuals who got fucked over can always move or change industries, like I did. "Nobody was forcing them stay," said still-leaning-Red me.
Then came the double-whammy. I already had a seizure disorder, but it got much worse. Then I was diagnosed with a host of intestinal health problems. All of this, by age 28.
It threw my entire existence into upheaval. Suddenly, through no fault of my own, I was incapable of holding a job for more than 6 months. On and off unemployment and food stamps. Taking out Title Loans and selling cars with liens on them just to make ends meet. Had to use the Medicaid expansion as soon as it became available.
As for employment... They say they're not firing you for being sick, but let's get real: They don't have to give you FMLA until you've been there a year, so their smart move is to chalk it up to attendance. Sure they take the hit on unemployment, but they don't lose a week of productivity at a time because I'm in the hospital, AGAIN.
So between seeing how the poor and middle-class are fucked over with my own eyes, living in a place that had zero public works, and being stricken with often-crippling illness... All within a 2-year span?
I already disagreed with Republicans on social politics, and found them lacking in fiscal discipline. But losing that hardcore Ayn Rand ideology meant I literally have no reason to vote Republican ever again.
Dillard, of course, was the exception. Still pissed about that.