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.