Similar to how google asks for a phone number eventually as a back up convenience in case you get locked out, would dong the same with email make sense? That seems like it would build trust and give the user control over their own risk.
According to your quiz, I have nothing to hide, but I'm still a strong privacy advocate. Privacy to me is all about context and understanding the consequences of your actions. If I run naked through Times Square, I shouldn't have any reasonable expectation of physical privacy, but if I whisper to a friend I would. Either way the important factor in both scenarios is that your expectation of privacy aligns with reality.
As for context, specifically with regards to prism, if I dial a wrong number that happens to belong to a terrorist, I may find myself guilty by association, with the burden of proof of innocence in my own hands. Quickly hanging up and dialing a similar number after might not be sufficient defense since that could be a strategy terrorists use to cover their tracks.
Aside from the insurance coverage, Airbnb appears to reduce risk for involved parties by humanizing the transactions. They encourage getting to know your host, and I'd imagine people are more likely to respect other people's property when they are aware of and can relate to the person behind the space. Even before transactions take place, users are encouraged to have rich profiles and social connections to demonstrate reliability and facilitate trust.
There may be potential for this sort of humanization in other areas where the perceived risk of a transaction currently outweighs the benefit. One way to think about it may be to consider things that you borrow from a friend. Airbnb covers the sleep on a friend's couch/spare bed niche quite well.
Some interesting things I can think of... perhaps using space on a more granular level such as holding a meeting in a conference room or watching a movie on a home theater system. Things like renting parking spaces might be interesting as well in some areas where parking is very limited.
We've reworded the message to mention acquisitions as well for the time being. We're working on better ways to display the information to convey a sense of caution and encourage further reading rather than the feeling of danger associated with the direct sale of information.
If the site's privacy policy explicitly states they will never sell your information, it may be possible to sue if they do so. There is some precedent with a toysmart.com case back in 2000, though it was settled out of court.
The main point of checking for the bankruptcy clause is to raise awareness of the risks involved so people can make an informed decision before trying a new site.
I wouldn't say it's too late. As with any adoption of new thought processes, you'll face a few challenges in overcoming conflicting ways of thinking if any, but it is definitely doable.
Here are a few "How to" guides with references to other resources that I've found helpful from my time scavenging hacker news:
I generally do better with task oriented learning, so I find it helpful to have something specific that I want to build, but everyone has a different learning style. Either way try to have fun and enjoy the learning. Good luck!