25 here.
My fiance and I went to a state school with very low tuition, and both worked jobs while there. While in school we didn't spend much money, and instead of partying, spent our time bettering ourselves at our respective crafts. We both graduated without debt, packed up my car (already paid off, low cost craigslist car) and left for a major city. We both found work soon after as a result of having spent so much time in school practicing and studying. We parlayed that work into more work, eventually started contracting, which came with higher pay, but lower job security. This was okay since neither of us particularly liked working at any given place for more than a year, and allowed us to move based on other factors. We continued to save up, and after a few years, moved to a much more affordable city in the Midwest, where we both found more work, at the same pay, but now with a much lower cost of living. We are continuing to save so we can put a down payment on a very reasonable, small house. Eventually we would like a small house somewhere out in the PNW, where we can have some farm animals and grow some crops.
Many of the people we went to school with couldn't find work after school. They didn't take school seriously, and as a result, were passed up in the job market. Many of them also had somehow accrued a large amount of debt, even with our modest tuition rates. The constantly complain about not being able to find work, but spend all of their free time watching television or doing something unrelated. I often see them talking about how the "industry is dead" or that the people with jobs are only there as a result of nepotism.
Many of the people we worked with had crippling debt, but still spent their entire paycheck without fail. One guy was bragging about how he bought a FLARE GUN. He had no use for it, but "just wanted one for fun". Same guy had almost 50k in debt and his parents were paying his cellphone bill and rent. We worked at a large tech company, making way too much money to have your parents paying for that kind of stuff.
Sure, we are not as mustachian as some. We do eat out occasionally, and I probably drive my car at times when I could bike. I am putting away close to half of what I make however, and this percentage should go up again here soon. We don't buy a lot of stuff, and don't have any recurring monthly payments outside of some work software, rent and utilities. Nobody knows this about us, and it isn't something I go around broadcasting to everyone else. I do have friends of a similar mindset, and we discuss these topics frequently. My guess would be there is some sort of conformation bias, and people are seeking out millennials who have made poor financial decisions, and saying, "Ah ha! They all must be doing this! What a crappy generation!" Social media platforms have also made it easier than ever to brag about your poor life choices.
So I wouldn't say that millennials can't get ahead, but instead that there are always people who will make poor decisions that prevent them from getting ahead, regardless of generation. Not having lived in the past, I can't say if things would have been easier or more difficult, all I know is what exists now.