Out of curiosity, what was insurance on you're first vehicle (or bike if you started @20 or below); and what was your income @20?
To be completely honest (and I've mentioned it here before), my first bike at age 18 was a 1983 900cc crotch rocket. I was bent over for north of $400/month back then because my record had a blemish on it as well - had it not I'd have probably been around $300/month. BUT, my income was healthy and my expenses (at the time) minimal, so I could afford it. I did get a quote on a ~400cc Honda of some sort (I forget exactly) and remember it being around $100/month...but in the end I could afford the 900, so I went with it instead. My insurance in the last year I rode it was about the same as the 400CC Honda would have been in year one, so it did get a lot better even before I turned 25.
This is open to anyone over 45. The days of landing a career worthy job and all the benefit that comes with, straight outta high school are long gone. Want to buy a house, car, motorcycle @20? Good luck. My old man managed all of that in mediocrity. But hey, today's youth are all just "a bunch of cry babies"; coming from the generation who arguably had it best of all, particularly in the last 100 years.
Friend of mine just went and got his class AZ licence about a year ago and is well on his way to making $50,000 this year, with benefits. We have guys making well over $100K/year at our company. I do OK myself as well.
It can be done if you're willing to accept the jobs that can do it for you. A lot of people think driving a truck or the trades are below them though, or hey, I understand it's not for everyone..but there ARE jobs. There IS good paying work....right out of highschool.
And not a lot more education can also put you into a whole different set of trades based careers. My son graduated from college this spring from a 1 year welding foundations course and is now working in his trade, will make around $35K this year (not stellar, but entry level position with zero experience) and inside 2-4 years will be very likely be making $50-$60K/year. Once he's red seal the sky is the limit.
But of course, like driving a truck, a lot of people think the trades are below them. So they don't bother to consider them at all, or go to school and take some useless course/degree in something like art or philosophy...and then complain about how they can't afford to live.
I will agree that the days of falling into a high-paying job right out of highschool without any effort or even basic training are indeed gone, but with not a lot of effort and some willingness to consider careers in which there ARE opportunities, I'd strongly disagree that it's impossible to do well for yourself without a degree or doctorate in something.