SSL is terrific for things that need to be secured, but there are a lot of web sites out there -- an arguably increasing number given the rise in popularity of static site generators -- that derive absolutely no benefit from being served as HTTPS rather than plain HTTP. Not "modest" benefit, not even "negligible" benefit, but no benefit. I've built relatively large sites that are entirely archives. They have no logins. They have no forms. I am not sure why it's "incomprehensible" to you that I'm less than thrilled that Google has decided I'd damn well better make sure my publicly accessible, 100% static, entirely form-free web site is served only over SSL.
I'd describe Dave Winer as more of an iconoclast than a crank, from what I've seen. But his point is that an awful lot of the Web As It Exists is unsecured, particularly the older personal pages and sites that are still hanging on, and that if Google decides that Chrome will simply no longer browse to unsecured web sites -- or worse, that their search engine won't just deprioritize but will delist unsecured sites -- a lot of the web will be effectively lost.
Do you drop tracking cookies or scripts that fingerprint the users visiting your site? No? Well by resisting the push to TLS, you're allowing ISPs and who knows who else to inject that content into the sessions of your users.
I'd describe Dave Winer as more of an iconoclast than a crank, from what I've seen. But his point is that an awful lot of the Web As It Exists is unsecured, particularly the older personal pages and sites that are still hanging on, and that if Google decides that Chrome will simply no longer browse to unsecured web sites -- or worse, that their search engine won't just deprioritize but will delist unsecured sites -- a lot of the web will be effectively lost.