> They walked right into a big problem because convenience or apathy about risks trumped everything.
Well, or just lack of knowledge, and lack of knowledge about lack of knowledge. I think from our positions it's easy to overlook that. Sure, it seems like people are becoming more technically literate, and they are, but I think when it comes to knowing what you can do, and knowing what you should do, the latter comes well after the forming in almost all exploratory loarning (which internet usage mostly is). We've heard the historical stories (myths), that impart this knowledge. Usually we've lived a few cases of it as well. Even then, it doesn't always take right away, or we get caught out not heeding our own advice. I can't fault a largely novice internet populace for not having had the same conditioning we have.
That doesn't mean they are off the hook though. You're right, there's a shitload of ignoring the signs in favor of convenience and general apathy, it's just not the entire story.
> If anything, history has shown we have to use things like regulations to force market participants to behave more safely on average.
I agree with regulations. I just vastly prefer them to target the specific problems and not try to get too complex with mechanics. Sometimes that requires really looking into the problem, and it can be a hard sell if the general audience for choosing/voting the implementation doesn't have enough knowledge. In this case, I think a lot of the problem all stems from using personal information as currency. Strong regulations on the collection, notification, maintenance, and ability to force removal of personal information by remote entities would make what the real cost is of the systems obvious (you know what they collect and how it's used, or in some cases you know what actual money you pay since that will become a much more viable model again). Open source cometes well in that market, because the actual costs are all apparent instead of hidden.
> We probably need a way to quickly present that when they make these choices.
I have hope this is a problem that will be mostly solved through the normal way societal best practices are passed down, from mentors (parents, teachers, trusted authorities). We just need to get to a point where the mentors actually know this stuff, which requires time and them being bitten by it and learning the hard way, or reading about those stories, or eventually learning it from their mentors. When your Mom or Dad is usually the one that cautions you at an early age to beware any free service that might be trading on your personal info, we've reached a good equilibrium (but we'll still have issues with those that don't have as much access to mentors, which is a constant societal problem).