When I drill a stock for pillars I don't use a regular drill bit but instead I use a piloted counterbore tool, it centers itself on the screw hole and makes it really hard to screw up the holes. You also need a pretty solid set up, if things move while you are drilling it can cause all sorts of problems. Tearing chunks of wood out is usually caused by a dull tool, incorrect spindle speed or movement of the work piece or a combination of any/all of these. Like the previous posters have said, you should be fine with a little extra bedding compound. Be sure and post some pictures when you get finished with your project!