CNET's Matt Asay wrote a great article about what he calls the "web's crisis of trust." Basically he says that Internet commerce is not where it could be, because people are scared to make online transactions due to concerns about security. Can you trust a faceless user or retailer with not only your credit card info, but that the product will be what you expected?
Asay cites eBay, which uses their feedback system to regulate "trust" instead of high-level rules and regulations. I use eBay all the time, but I would bet that every one of us was hesitant to use eBay at first, because you think you're going to get screwed.
It's not just retailers we fear — what about Craigslist? When I moved to San Francisco, I used it to find roommates, a job, and furniture online. My family was scandalized that I used this impersonal web board to meet up with people — claiming that I didn't know what kind of weirdos were on there. Well I do know those weirdos, because now they're my friends, former roommates, coworkers, etc.
I often muse that if I had suffered from this "crisis of trust" with Craigslist, I wouldn't have what I do now. So, tell me, has a crisis of trust with the Internet ever kept you from buying or doing anything you found there?