Again, I'm no expert. Answering to the best of ability FWIW.
1. Use it. I wouldn't bother trying to scrap it off. You might gouge out the leather.
2. Sharpen the Crown on the Sharpmaker and use it as your beater/learner knife for sharpening and stropping.
3. Rough side removes a little more material then the smooth side. The smooth side is more a polish step.
4. Compound comes in 4 colors. This is a *generalized* statement about compounds.
Black = all cut no polish, White = cut and polish, Green = little cut more polish, Red = no cut all polish
5. Strop texture + compound work together. It isn't really one or the other although you can strop a knife with no compound on the leather. It's kinda like brushing your teeth. Just using a toothbrush (no water or toothpaste) will help clean your teeth, but the toothpaste adds some grit to help scrap off stains and polish your teeth.
Don't think just because you have a strop, you won't need to use the Sharpmaker or stones. Stropping is part of the process for sharpening a knife, not the entire process. How often to do it? It depends on how often you use your knife and what you cut with it. 7 hours of breaking down cardboard will require stones. 7 hours of cutting tape... some cleaning and stropping will probably be good enough.
I've heard that depending on the use (as you said), stropping might just be enough. By that I mean I think I only would need to use the Sharpmaker once a month and strop once or twice a week.
EDIT: premature post...
Let me explain. On average, I probably do a combined total of 1-2 hours breaking down cardboard a week with some tape cutting and letter opening sprinkled in there. Oh, and a little paracord cutting since I just started learning how to make my own lanyards/fobs. As you can see, very light work.
I know a lot of this depends on the steel as well, but I'm essentially trying to limit running my blades through rods as much as possible. I think I can achieve this with the amount of actual cutting I do, if I get my strop technique down. (At least that's what I've gathered so far from the internet.)
The thing I've learned is that a strop is good for between sharpening and that if you don't hone the edge with a stone, a strop will not be effective. Depending on the steel, for some knives a strop between sharpening really doesn't do any good. I use a ceramic rod and strop for in between sharpening.
Not sure what honing is exactly. And the steels I have are 9CrMoV13(sp?), D2, S30V, and S35VN. So, I
believe that most if not all the knives I have came with great factory edges (Cold Steel, CIVIVI, Spyderco, Kershaw). They all came shaving sharp. Forgive the ignorance, but, are you saying that even if the knife came shaving sharp, I should still "hone" the edge with a stone before stropping?