The most important thing I take away from Marc's post is the realization that, in naturally enough concentrating on my subject, when my eyes decide it's "in focus" I may very well be failing to observe that a foreground/background item might be
more in focus. Anyway, I've found that putting the O-me53 magnifying eyecup on helps a bit. (partly because it allows easier access to the diopter adjustment
)
Looking at the OP's photos, I wonder whether trying this might help: When I'm not sure of focus, sometimes if I can concentrate on a small highlighted area - for example, a highlight on one of the peoples glasses, in this case, or the highlight in someones eye, and I try to get them as "undiffused" looking as possible, this helps more than trying to perceive "sharpness." Or if there's a small piece of text, a sign for example, in the plane I want to focus on, I look for the loop in a letter "e" for example, and try to get it as "tight" as possible.
All this because I'm too lazy and cheap to get a KatzEye.