When was it ever otherwise? Sounds like you had it pretty good compared to the previous generation at the same age. Better still than the generation before that. How "easy" does it have to get before the perception will become that it's not hard?
I see the problem as one of perspective. Unless we've actually been through tough times, we feel we're having a tough time.
Same for unemployment benefits. Stories from the 60's and 70's show British counterculture surviving pretty well on benefits. When I did a 6-month stint of unemployment in 1990 it was still possible - the state paid my rent and enough money to feed myself and buy cigarettes and a few beers. Now it's a brutally harsh life on benefits.
I know that's only examples of state handouts, but it's an indication of attitudes. Again, when did we get so convinced that life had to be so tough?
I'm pretty sure the divide is now razor thin: either you're pretty rich, or poor...
To my recollection, it's always been the case that the first few years of employment after education come with harshness due to lack of experience. Maybe you had to live with parents for a couple of years. Maybe you had to use a friend's couch for awhile. Maybe you had to work a menial job for a bit. Just because one has graduated with a degree doesn't automatically entitle them to the nice apartment overlooking the beach and a sip of a expensive bourbon every night.
I suppose in my corner of society, things are indeed better with each generation. (I'm nearly certain we've never had a safety net quite like you describe in the UK in the 60s and 70s.) It's not that "it has to be tough" it's just that "it's never going to be easy." And without some perspective, "easy" is not so objective.
That's not the same as what we're hearing from the millenials. We can choose to write that off as the whinging of an "entitled" generation. Or we can choose to listen to them and compare their stories to ours.
Talia made some mistakes. That's what your 20's are all about. But she's working a full-time job and is unable to eat properly. I don't think that's acceptable.
By writing her off as an entitled whinger I think we're putting our hands over our ears, going "lalalalalala" and ignoring a real problem in our society.
Even during the dotcom bubble there was a sense that this would be good for everybody. Obviously that was nonsense in hindsight. But now people have totally given up on the idea that things should improve for all of us. If you somehow didn't luck into the right job it's your problem that you don't make money.
Programmers watch out: Right now we are riding high but our day will come too when people will tell you "Who could be so stupid to learn coding.".