I agree with the caveats you outline, though. I think to work, something like this would need to be a box you'd tick when signing up for your ISP that promised some "ad free premium access to [X number] of sites" or similar, and you'd trade entirely on it being big name sites. Even then I'd expect relatively limited takeup mostly from people unaware of ad blockers.
How many people would sign up for a 15$ per month subscription to read one article with no ads? How many would pay 1¢ once to read the article with no ads? How many would sign up for one 15$ per month subscription to see no ads anywhere?
I realize we don't have the infrastructure to make high volume 1¢ payments, and probably not for lack of trying, but I just don't think the core problem is that people only want stuff for 0¢ and not almost 0¢.
I'm aware I'm preaching to the choir here on HN, but boy are there strings...