I was in the SF Bay Area and spending $1600/mo to rent a studio apartment in my 20s, and even that looked like a bargain compared to the people that graduated a few years after me. And my starting salary was probably higher than your friend's when adjusted for inflation, but not by much.
Not saying it's right - the US needs to do better when it comes to affordable housing. Just that expensive housing is not exactly a recent phenomenon, and your friend's situation is not hopeless.
You could easily get away with a "gap year" between school and starting a career, but multiple years of screwing around seems pretty hard to come back from. There are exceptions of course, but I can't think of many. One relatively recent example was the rise of coding "boot camps" - where I know of several people who were able to change careers and land high-paying gigs. Or the more traditional path would be serving in the military, getting a free college education, and then going on to a successful career from there.
Has it actually gotten harder to do that recently? It would be tough for me to say without some data. Certainly any time the job market is tight, and there is strong competition for jobs, it's going to put non-traditional candidates at a disadvantage and make it harder to change careers.
As a boot camp graduate, you really have to either be extraordinary or know the right people. College doesn't just give you education, it also gives you references and a network, something that many boot camps lack.
> serving in the military
Nothing against our hardworking soldiers who put their lives on the line, but I would not fault anyone who does not want to serve in this particular military at this particular time. I don't expect it to be like this forever, but it does put today's young people in a predicament.
> free college education, and then going on to a successful career from there.
People with advanced degrees (paid or not) are having trouble finding work, even with masters in STEM fields. Entry level jobs are diminishing. Yes it's hard to change careers, but seems even harder to start one these days.