If you come from wealth, it's easy to get into a good school, and your parents can subsidize you while you're launching your career (or outright create a career for you).
If you don't come from wealth, and you get to a city, and you start making over $200k, it's hard to even take advantage of it.
Instead of having parents to subsidize me, I have parents who are pretty broke and in bad health. How can I justify buying a modest house in my area (for $1M), when my parents are piling up debt, struggling to pay rent, and barely able to buy groceries?
Flip that even further to people who come from really poor countries like India. I can't imagine if my parents were working $1 an hour -- how could I pay $3k in rent? How can you invest thousands of dollars in yourself when your parents don't even make that much in a year?
But if you don't make those investments, you're never going to get ahead...
It's not just that wealthy millennials have a huge advantage, but coming from a poor family has a HUGE disadvantage in terms of social mobility as well.
Is this a moral conflict, i.e. you don't feel comfortable spending that much money? Or you're actually giving so much money to your parents that you can't afford to buy a house?
For example, my down payment could buy my Mom's house, my Dad's house, and my brother's house. The conflict is -- how can I spend that much money on myself? Instead, I could retire both of my parents, and set my brother up for success at the cost of continuing my current life as usual.
It doesn't seem like a huge burden to me to continue my life as usual. And it would be completely life changing to the rest of my family (the people I care most about) to allocate my money in a different way.
On an infinitely smaller scale -- this is similar to the Bill and Melinda Gates Foundation. How much money should you invest now to help people in the future vs giving people money now?
When I was 20, I was giving my family 10s of thousands of dollars a year. The cost of that was that I delayed my career advancement to the point I could be making an extra $100-200k per year now. Sure, I'll get to that point in 2 years time.
But was it really worth it to spend $30k to pay for some weddings and refrigerators and medical expenses 8 years ago to miss out on $300K+ in earning potential over that time period? No. Definitively.
Is it worth it to give my family $200k now when I hope to turn that into a million+ in 5 years? I don't think so. How do they see it? Well, they want the $200k now. Maybe that type of vision is why we're in different situations. Who knows?
If I were in your situation, I'd want to secure my own family's housing and retirement at least as much as your parents' housing and retirement, so as in many things, balance is going to be key. But if you truly value changing their lives at the expense/delay of your own, there's nothing stopping you from doing it and obviously nothing wrong with it. It's a very personal choice.
Where exactly are you investing $30,000 that returns more than 100% / year for 8 years?
The opportunity cost of doing things when you're at a low wealth level is enormous.
The obvious example would be to consider the gap between being homeless with $0 and being homeless with $5K.
Your earnings potential just essentially went up by an infinite amount because now you can rent an apartment, get a job, perhaps buy some study equipment like a computer or whatever, and suddenly that $5K can be well north of $50K.
This isn't stock index tracker stuff, this is home economics.
I finally break 6 figures and my kids are almost graduated into college. If I left them behind after the divorce I could literally blank check pay for their college.
But I'm deciding to be their dad instead of chasing the money. But 3 more yesterday the last one graduates and I'm ready to go do machine learning and all the fun stuff. So. Sick. Of. Web sites.
I would recommend you let your family be. There earlier stuff in your career was health problems you said and people come first. The houses you talk about now are like gifts. They don't have immediate need so you can get them something better in the future.
And just how hard is it to reach your level btw? I've been programming twenty years... Is it hard to get a job after 40?
And if you are making huge amounts of money it's completely reasonable and rational to spend it to actually increase happiness and opportunities, given that one cares about people around them.
Getting that job in that major metropolitan area and actually going to work every day in that job carries such incredible direct and indirect costs, by the end of the year it’s typical for most people to be worse off than when they started.
This is to say nothing of the opportunity cost of all that time.
Then finally, if you are willing to factor in the societal/cultural pressures that come with the job and the massive costs associated with fulfilling them, as supposed to just calling that weakness on the persons behalf for succumbing to those myriad pressures... well, as you alluded, the tail is most certainly wagging the dog.
It's all good in your 20s, when you're in good health, and when it's easy and cheap to make friends. Then you hit your 30s and find out that you don't have any community, everyone moved somewhere else, the city is too expensive for a 2-3 bedrooms flat, and even if you stayed you'd have to work full time (if not overtime), which means you'd need someone else to bring your kids to school and take care of him/her after work, which isn't free.
It's a lot like the "get a loan to buy a car, buy a car to go to work, work to pay the loan" analogy. It's not a life, you merely exists for work and pay other people to take care of what used to be the core experience. At the end of the day the only thing you're looking for is a meal and this new netflix show your heard about.
The worst part is, as you said, that it's now frown upon to rely on your community because it's "free", and surely you haven't made it if you rely on free things.