This is a great thread. A few comments:
Affordable housing: In most of the developed world, a starter home is a 600 sq foot flat in a high rise in a city close to a metro station or walking distance from where you work. This actually works a lot better than the American sprawl model IMHO.
College Costs: An embarrassment. What's amazing to me is that we still have a shortage of plumbers, electricians, welders, and other skilled trades when the costs of attaining those skills are minimal and the earnings in year 5 onwards are more than the average college graduate.
Status vs. previous generation: My parents were good enough to give us kids a head start by paying for undergrad. I committed to my kids I'll do the same and I am. Some will call this privilege. I agree if it's abused. I've worked my tail off to not abuse it as a way of showing respect to my parents for the amazing gift they gave me 30+ years ago. I hope my kids take the message or the gift the same way. I continually tell them that not everyone is so lucky and hope they understand and respect the situation.
Boomers: took us a long way. My "Gen X" generation still seems to be outnumbered. The Millenials are louder and we need to see what they do with their power when they get it. I fear that a lot have had it too easy and don't have enough international experience to see the long term effects of socialism. They should all go to France and and understand that for most people it is essentially illegal to earn more than EUR40,000/year because to do that would require working multiple jobs or overtime and that is not allowed. Only when you live it and see it can you understand if that is a way of life to impose on a society.
Getting ahead: All starts with saving and avoiding debt. I saved 25% of my first paycheck and at least that much of every one after. I got into the debt cycle for a while but have been completely debt free now for 5-6 years. It's powerful.