I'll say this, then I am done.Every generation has had those problems. When I first went to college, income based payment wasn't a thing. Instead you had loans that couldn't be discharged in bankruptcy, AND, there was no reduced payment.
Can't afford it? Tough cookies, we're garnishing your wages, and taking your cars and houses for delinquency after going to court.
You don't have to deal with that. EVER.
Medical bills without insurance? Sure, but a bankruptcy fixes that, IF you choose to go without in the first place. I know plenty of people (not all mind you) who plead the arguments I hear here but have to get the latest iphones, or 120/mo cable TV package, xbox live gaming pkus internet packages...and all other kinds of "luxuries" the rest of the world has done without through history. Either you're so so poor without assets there's low income state provided care, or, you make it a higher priority. Even the Starbucks craze, or a lot of the food kids eat... man, spam as part of a meal to replace meat that was too expensive just ain't even a thing anymore, don't get me started on that.
(I do agree with base depreciation for certain makes and models... otherwise wed all love to have that aston martin and ferrari parked next to a Cummins diesel in the driveway. supply and demand, it's always been like that too, not just recently.)
Very very little of what we considered as was "fun" in my days in the 80s/90s is a felony today. In fact, I really can't think of one example?
And news flash.... crazy girls have been a thing as long as there have been girls. Not a new phenomenon. ; )
I forgot all the parks and fields were privatized and closed. We used to have 20 kids show up with one ball and play for hours. Maybe that's been made a felony too. Or bike riding. Or dropping $20 on a fishing license? Kids can be kids if they want. They just aren't interested unless it's new, trendy, and expensive.
FWIW, there's generations beyond the boomers in the military. Luckily, there's enough non-cry babies to support minimal staffing. Although, there IS a legitimate talent shortage and problem with fitness standards and new recruits vs earlier years...
As far as student loans go, that problem is just as bad now as it was then. Those debts will still haunt you forever, plus as long as you have them you cannot get a loan from the bank for anything that doesn't have it's own equity for fear that you roll whatever money you get from the bank into the student loan debt and then file bankruptcy to clear the debt. Add that to the relaxed interest rate controls on student loans now, and you can be screwed for most of your adult life pretty quickly.
As far as medical debt, it would cost me about $600-1000 a month for personal health insurance. I don't think doing away with cable and XBOX Live is going to fill that hole in my budget. Not even skipping the avocado toast is going to do it. That is like buying a brand new iPhone every month for the rest of your life.
As far as felonies go, drag racing your friends with that project car is called Reckless Driving now a days. Booze cruising is called Underage Drinking and DUI. Maybe you and your friends did none of these things, but a lot of others did.
Also, we live in a day and age where a girl can say that you sexually assaulted them with no proof, and if you can't conclusively prove that it could not have happened, you are going to jail. If you still can't prove that it didn't happen at trial, you go to prison. Laws these days make dating a borderline dangerous proposition.
As far as outdoor activities, you can blame years of helicopter parenting and telling kids that every person they meet is a pedophile and a murderer, and that anywhere out of Mommy's sight is a scary place.