Trey,
I sand as little as possible.
More seriously, you generally want to avoid using a power sander on the otherwise sharp edges of projects unless you want to round them over. I almost always do that but I wait to use 220 grit, normally the finest I use. A little bit of chamfer or round over is normally a good thing, especially on something like a drawer. I don't mark with a pencil, maybe I should, but I do try to give the projects about the same number of passes with each grit of paper. I start with 80 or 100 depending on how much I think I need to remove. Then I count how many passes I give the sander. Then when I progress up to 150 and then 220 I give it the same number of passes. That works well for me to allow each grit to get rid of the scratches from the previous grit. You may also want to use a light at a low angle on the piece to look for scratches from the previous grit. I also use dust collection when possible both for the sake of my lungs but also because I think it makes the sander work better.
On something narrow, like the edge of a drawer or table top, it helps to get the piece oriented well, clamped down if necessary, and to be careful to have the sander horizontal so you do not bevel the edge. At first it might be better to hand sand the edges. It is easy with a power sander to bevel a 1/2 inch wide drawer side. A hand sander is also a safer way to gently round over the edge after the piece is essentially sanded.
I make no allowance for what I remove with sanding when sizing something like a door or a drawer. If you do it right, the removal is minimal. It should be less than 1/64th. But if my drawer sides are glued up, I will do initial sanding before cutting to final size. That's never a bad idea in my opinion. If you resume sanding with 150 after you cut to size it further reduces the chance you will take off too much.
Jim