If an option then system provides is self-destructive, maybe it should stop providing that option?
Some people don't even have $10 per month spare. Wealth inequality in the USA is extreme. But more importantly: they are busy and stressed. If it's so easy to get health insurance it should either be mandatory and automatic, or it should be a checkbox on your taxes or some other form.
When I paid my student loan it was a matter of just ticking a box on the employment tax declaration that I had a student loan. And then it was automatically taken from my paycheck. It wasn't about the money, but about the ease of use. If I had to send a monthly payment with a paper check I'd surely miss payments.
The phrase "personal responsibility" is a thought-ending cliche used when someone doesn't want to see the big picture. It's like if Microsoft changes Windows 12 to break Valve games and you blame the game because "developer responsibility" or "executable file responsibility" and ignore the bigger picture that Microsoft is trying to drive Valve out of business to move games off Steam and onto the Microsoft Store.
The ACA is about a 10 to 20 minute process, once a year, on a website. The average american of working age, employed, watches 120 minutes of TV a day. If one day they only watch 100 minutes of TV, they could have health insurance. Again, how much more handholding do people need?
For loan payments, somehow generations managed to pay mortgages, property taxes, and more with nothing more than a checkbook they manually balanced and gasp paper, envelopes, and stamps. Again, even if you have to log into a website to manually trigger an ACH, put a recurring calendar event in your phone and include a link. I bet you could get that down to 3 minutes a month, assuming they don't have autowithdraw.
Your Windows/Valve example has Windows taking action to make things harder for people. All the examples you provided are things that are easier now than they ever were in the past.
Even your initial premise that these options are inherently self-destructive is wrong. If you're a trust-fund kid and want to study art history for $100K a year, great! We shouldn't take the option away from everyone just because some people rack up $200K of student debt. We shouldn't further bureaucratize and regulate the healthcare system just because some people are too busy (read: watching TV) or stressed (read: can't follow instructions written at a 4th grade level) to work through a few questions on a website.