To cut out a little confusion forget about the terms for a minute and think of everything as sharpening. The bull leather you have should be mounted to a flat piece of wood to start, if you want to use it dry then that is your choice but I use mine with the diamond spray and really like the results. The main reason I use leather for stropping (stropping relates to action your perform with the leather and compound or honing film, edge trailing) is because of the "give" the surface has. When you sharpen by hand your bevel is naturally convex simply because you cannot hold a perfect angle, the leather conforms to the slightly convexed bevel and blends it in a single stroke rather than multiple strokes across a flat surface, this also adds to the convex shape of the edge and breaks the shoulder of the bevel.
I like to think of honing and sharpening as the same thing (ie. using a stone) and stropping is the edge trailing method used with leather, wood, honing film, and micro abrasives. Before you even get to the point of stropping the edge of your knife must be refined and already have a acceptable level of polish, the burr must be minimal and the edge itself in proper alignment. The burr will be easiest to detect if you strop/edge trailing the top of your finger nail, if their is a burr even a very small one it will scrape the surface of your nail. You will be able to detect the size of the burr by how much it scrapes the surface also. Once you feel that the burr is small enough make about 10-20 passes per side on the wool pad before moving on to the leather or honing film, this will help to "break" the burr before you move to the leather and honing film, if the burr is too large it can actually damage your strop.
When you start with the 1 micron spray you will instantly notice within the first few strokes that the knife gets much sharper and becomes almost burr free. You could stop at this point but the only thing you have done is align the burr straight and not really removed it, from your count it seems as though you are doing enough strokes but you might not have the edge to the proper point before moving to the strop. When you are getting close to finishing up on the 1 micron and get ready to move to 0.5 the edge should be burr free and very sharp, though once you start with the 0.5 micron compound the burr will probably pop back up. This happens for the same reason it happens on a stone, by changing grit/mesh your starting a new scratch pattern and as you work-in the 0.5 scratch pattern the burr will go away again. If your edge is not mirror like, smooth/sticky when you touch the edge, and sharp as a razor by the time you finish with the 1 micron compound then you have done something wrong.
I hope this helps a little.
P.S. Instead of 50 this side and 50 that side try alternating 1 stroke per side.