...I tried the table-top idea.

That seemed to help reduce the "droop variable" as you put it, however the handles at the end have these riveted buckles coupled with the fact that it's a double sided strop (so underneath it was the cotton side) and that caused a slight droop as well. Nothing major, but still.

As I was stropping, perhaps it was because my eyes were fixated closer on what I was actually doing (as opposed to just "going through the motions") I noticed a tendency of the edge of the blade lifting up.

This happened going back and forth. And this seemed to happen more when I was allowing the weight of the SR to be the only pressure I put on the blade. Then I tried a different approach. Using my right hand to sway the SR back and forth, I used my left hands index finger and middle finger (spread apart) to cover the top & bottom edge of the blade to ensure they were making contact with the strop, as I was stropping.

Keep in mind, I wasn't pushing it that hard; just hard enough to make sure it was making contact at least. Keeping in mind everything I saw on the video (The World of Straight Razor Shaving) and everything I read online, I didn't feel comfortable at first doing this because Lynn says to not put any pressure on the blade. But again....when I did it that way, the edge kept popping up along the strokes.

Doing it this way was definitely slower (much.....MUCH slower) but at least it made contact. As for the sharpness? Well it seemed to be sharper.

Then again...maybe I'm just thinking it made a difference doing it that way (the placebo effect, if you will).