Excellent info so far!

IMO, It's super easy to roll an edge with stropping, and it's mainly due to pressure. As the edge becomes more refined, it becomes thinner, much like peeling away the layers of an onion. The edge of the edge is fragile and is easily prone to being flexed when lateral forces are applied, even if it should readily spring back into position.

Geometry plays a role in the strength of the edge, but ultimately, you still want the edge to be thin enough to cut effortlessly.

As mentioned previously, the steel's qualities will also play a role in how much pressure an edge can take before becoming fatigued or rolled.

To add one more thing, by the time you get the the strops on the WEPS, you should have one seriously well defined and sharpened edge, so you won't need to add much pressure at all - especially if you take the time at the finer WEPS stones/plates (or Choseras and Shaptons

Hi again Lucky
I can only speak for myself, but I have found that I don't count strokes...