>>> The security treadmill is hard for even the most modern tech companies to stay on. I think the infosec community could go a long way to helping itself by making easier to use tools, and writing canonical guides for common scenarios. Setting up HTTPS to get an "A" from SSLLabs is non-trivial. Securing SSH with perfect forward secrecy is near impossible for a mortal. There's no reason it has to be this complicated.

Agreed on this. Security is too hard to do right and too hard to check. There are no 2 guides or 2 people that agree on the same recommendation.

SSL labs is a perfect example where the top rating is not realistic to obtain.