I always have a little powdered sugar left. One thing I found I was mixing it in too small of a bowl. When I went to a bigger one, it was easier to get the powdered sugar mixed in because I wasn't worried about spilling it everywhere.
Also with the trouble you are having with lifting the fondant after it is cut, I have a couple of things I do to make it easier. Is is also mostly why I like mine to sit for a week , if I can. It seems to be more pliable as opposed to being stretchy, if that makes sense.
I went to JoAnns and got a yard of heavy clear vinyl and cut it into about 12 inch squares. I grease the square with crisco, wipe it off with a paper napkin, put some fondant on to it, dust the fondant with a little corn starch, and roll the fondant with a silicone rolling pin. I bought the rolling pin at Bed, Bath and Beyond for $7. It is the kind that spins around while you are holding the handles, if you know what I mean. I do not like the fondant rollers with no handles.
Then I cut out the fondant, let it sit for maybe 10 or 15 minutes, using that time mostly to roll out and cut some more. I find that leaving it sit helps with the handling, it dries a bit and is more managable. The small vinyl square lets you kind of peel the fondant off, like a label, it doesn't distort quite as much. I don't do very many cookies at a time, maybe a dozen or so before I start the process over.
I use thinned karo syrup to adhere the fondant to the cookie. Have found that the thinner the better, straight out of the bottle is way to thick.
I brush it on with a fairly good size artist brush, bought at Michaels, not very expensive. When it is thinner, it kind of soaks into the cookie, doesn't make a mess on the fondant, but it still adheres very well.
I wouldn't roll it any thicker than 1/8 in, that begins to make alot of icing on a cookie.
I just roll my pearls by hand, it is easy and cheap. I think you will like MMF once you get the hang of it. It is alot of fun. Hope some of this helps.