Just an outside perspective. Your talking about how it's easy to be frugal when you inherited $40k, earn >$100k and never have to be actually frugal, you choose to be.
I hate buying gas and feel guilty about it, but also would like to be able to seat 6 people, so suddenly a Model Y seems "reasonable". But sitting down and doing the math shows that even if my goals are environmental, keeping the 12 year old Honda and getting a rental car now and then is much better than a brand new EV (and vastly cheaper) - but before thinking about it carefully, I was tempted.
A lot of people seem to have the idea that being a full-grown human is being rich. To me, it's being able to plug all the holes in your own roof and always bearing in mind that we're just here for a limited period of time, to gain knowledge and experience, not things to make us lazy and comfortable. But maybe that's just like some weird post-religious self denial predilection I hold onto.
I appreciate the attraction of the simplicity of older cars, but you are accepting that a crash could turn you into pink mist if you are lucky, lifetime of pain and disability if you are unlucky.
"But we must not follow those who advise us, being men, to think of human things, and, being mortal, of mortal things, but must, so far as we can, make ourselves immortal, and strain every nerve to live in accordance with the best thing in us; for even if it be small in bulk, much more does it in power and worth surpass everything."-Aristotle, Nichomachaen Ethics, Book X, 6
On the spectrum of all humanity, inheriting $40k in your twenties is on the lucky side, but it's also pretty basic. I wasn't born a Brahmin and I didn't exactly inherit Dubai. I also know a lot of people who were trust funders from birth and threw it all away, or blew their money on bad ideas. Or blew it up their noses and committed suicide - I knew several of those. Just from my own observation, most people who get money and don't know how to manage it are parted from it pretty quickly. This isn't to say I deserved to inherit something, just that, life finds a way to equalize out stupid behavior pretty quickly.
Reminding myself that that's the case is probably the only way for me not to go broke.
Not to mention that we're in a society that incentivizes people to be irresponsible. I'm not allowed to earn six-figures or I'll lose healthcare. Same with inheriting/having more than a certain amount saved. My meds cost 300k/yr, so I hit OOP max the first month of ANY health insurance plan I have EVERY year. The wrong plan can cost me over 20k/yr.