1. I have the outer skirt sewn to the inner of my costume so I don't know what it would be like any other way. I'm guessing as long as no one can tell the difference it should be fine to sewn it to the inner skirt. The only real time I have issues with stepping on my skirt is going up stairs.
2. I don't have a saber that is an exact match to the picture either, but as long as it is a KOTOR style hilt, meaning it closely matches something you'll find in game, I would think it should be fine.
3. I'm not sure about wearing pants over your boots. I suppose you're really only going to see the toes of the boots so it could probably work. That may be something up to you GML to decide.