In the context of e-commerce, I already have to provide a lot of personal information. So now it's credit card number (which may be autofilled + CVV2) vs string pasting into wallet. Based on current UIs, I think it's a coin flip on that one. Maybe browsers can improve cross-wallet management.
I was speaking about this article and the root comment. Overstock is almost entirely physical goods, and I'm skeptical that this has a meaningful impact on Bitcoin as a whole.
But your point stands re: digital goods. One use case I was thinking Bitcoin might be good for is micropayments of content. Replacing paywalls with a one-time fee to view the article or get access to the whole site for an hour/day/week. Cookie the browser with no registration. May be ideal for porn.
The challenge, aside from the lack of users that have Bitcoin, is that people don't like getting nickel and dimed. Sites may not adopt it because they can get more money from fewer users paying more on monthly subscriptions, versus more users paying less for one-time transactions.