HTTPSNow

Given the ease of obtaining a root certificate, I'd say nowadays they're a great deal less deceptive than some CA-signed certificates. Visiting a site that has a self-signed cert doesn't prove your connection is safe. Visiting a site that has a CA-signed cert doesn't prove your connection is safe. What's the point of this exercise again?

I'm not sure at all what your second paragraph gives us. We don't need a fourth party to mediate the certification the third party gives us. The whole process of cert signing is a certification from a third party. That part actually works; the problem is that browsers accept signatures from organizations they should not, and the meta-problem is that there really isn't a solution to that problem. (What cert organization is secure against their local law enforcement?)

I guess someone in a sensitive position (e.g. someone with access to the routers at a major ISP) could intercept a every bit of traffic and produce a similar result but it doesn't seem likely and there's a flip side to this argument which is it puts a financial strain on the companies themselves.

Wikipedia, for instance, surely wouldn't have the processing power to switch all its connections to https. So they'd have to significantly upgrade their infrastructure at an equally significant cost.