I think this is key.
In my opinion people CHOSE to make their life like that. There are alternatives. Nobody is forcing anyone to buy a house, take on huge student loans, or fall into medical debt. Culturally we like to tell ourselves that we don't have a choice but there is one.
What good is life if your whole existence revolves around falling into debt, and working to pay off that debt, followed by probably buying a bigger house and getting more debt, and so on? Why not utilize borrowed money to get ahead rather than constantly worrying about bills?
Even if travel isn't your thing, and you're into spending disposable income, it makes a lot more sense to live within your means, minimize your debt, and then buy lots of toys with your free time and money.
This might mean moving though. You need to be able to live in an area with respectable incomes and a real estate market that makes sense. The McMansion trend seems to be continuing and this makes buying a small home more difficult than before. We can all live in 1100 sq ft houses and have our homes free and clear in a relatively short period but everyone has to buy that 2300 sq ft place to keep up with the Jones'. This pretty much keeps you in debt for your whole life. Screw that.
I think the college & home mortgage ones are the most difficult. Statistically, you stand the best chance of being financially successful if you complete & attend college. And a big chunk of people want to start a family & have a home. You have a better chance of getting more job offerings & make more money if you finish college. But even local community colleges are getting super-expensive these days. There is the whole "Four-hour work-week" concept started by Tim Ferris:
http://www.fourhourworkweek.com/
The problem with that is that you still need people showing up to work every day, making stuff for you to use, so that 4-hour workweek program only really applies to a niche selection of people who can be mobile like that. It's a bit harder if you have 4 kids & need a steady income to cover housing, food, educational costs, etc.
But you have an excellent point, and it's a big problem in America: we don't live below our means & we carry a lot of debt. I think school, home, and car debt are OK because those are things you generally "need", but there are wiser ways to go about getting those - don't buy a mansion of a house, buy a reliable used car instead of a new car, etc. Basically don't buy what you can't afford.
Affluence is really a two-edged sword: yes, it's wonderful to have everything available, but on the flip side, it's really easy to get fat (= heart disease, diabetes, heart attacks, etc.), get in debt (= stress, jailtime, etc.), and so on. Lots of traps out there, no matter where you live...