I'm also a bottom feeder. If I'm doing a bunch of smaller holes, after drilling, I flip it over, sand, and then use a pointed awl to push all the holes in a little. If the holes are really tiny, I sharpen a point on the end of the blade, makes for easy entry. I also have a dedicated small LED light that shines accross the scroll saw table from the side, so I can see whats going on under there.
Pete