@jgrahamc: Do you think it would be feasible to add clearer notification about potentially creating a false sense of security to the Cloudflare ui, when no origin SSL is present? What Cloudflare calls "Flexible SSL" has real implications and I think one of the necessary evils of infosec work is pushing people towards more informed decision making.
As a frequent Cloudflare freeloader and occasional paying customer (lots of different hats), I really appreciate how the service made it possible to use SSL for free, before it was cool.
With Let's Encrypt being implemented at a lot of hosting providers and hosting automation systems over time, I think the following may become a diminishing problem.
But in cases where, let's say, a "not top tier" hosting solution makes it impossible to use any sort of SSL/TLS back to the origin server (within the customer's budget), my personal choice has been to not defaulting/redirecting sites to Cloudflare's SSL.
And I mean, it's not like crappy hosting without Let's Encrypt automation or the ability to add Cloudflare's origin CA, is going away. One of Cloudflare's selling points at the low end, is how the service stretches the capabilities and resources of less than optimal hosting and apps. I mean, the idea of running Wordpress without Cloudflare or a similar service in front, really gives me the heebie jeebies.
Not going half-way with SSL is sort of an ethical choice for me, exactly for the reason of not wanting to give a false sense of security, even at the cost of Google juice.
I'm technically proficient enough to understand that client -> Cloudflare https connections can stop a lot of ISP/last mile/LAN level tracking and code injection, though. And obvioulsy, Cloudflare is a MiTM. So it's a real choice with tradeoffs.
But I work at a grass-roots level where I usually am the only person tangible IT skills. When it comes down to it, I feel quite strongly that we should avoid messing with people's already vague understanding of what that "green lock" means.