Wow, I just revisited this blog from months ago and saw that I never responded to your comment. I take the viewpoint of "When, not if" because I consider it true, not because I like it. In fact I hate it. I hate that it's true because it is— as you said— the culmination of hundreds of policy failures all the way down. But it is realistic.

Believing "When, not if" doesn't mean I'm giving up. I will continue to wear a mask where feasible and take other precautions, including reducing my time in risky environments. I will continue to get periodic Covid boosters, even as it seems we're going to settle into a yearly booster pattern a la the flu vaccine.

There's an element of the uncontrollable, though. Despite these efforts I figure there's going be sometime when I'm in a place with a sick person and my mask and vaccine fortified immune system aren't enough. And that is when, not if, I will be sick.