First of all, the hole wizard is a great improvement over extruding a circle, but I agree that it needs some work. I hear SWX 2001 improves the hole wizard even more.
I am not familiar with a PEM Nut, but I think I know what your problem is based on this assumption -- you are trying to create the hole running through the cylindrical face of the nut rather than the flat face. If this is a correct assumption, that is the problem. The hole wizard only works on flat faces. In order to use the hole wizard (until SWX 2001 that is) you need to create a flat face on the cylindrical surface. Here is how I normally do it:
1.)Begin by creating a plane "On Surface," normal to the direction to create the hole. You may need to create other reference geometry to fully define the location of the plane.
2.)Sketch a small circle on that plane, the diameter should be smaller than the hole diameter you will be creating. Constrain that circle to the location that you want the hole.
3.)Create a boss extrude "Up to Surface" and select the cylindrical face to extrude to.
4.)Select the flat face of your new extrusion (it's not really a spot face, but I call it that).
5.)The hole wizard icon will be available and you can create the hole. Constrain the point of the hole wizard concentric to the spot face in order to fully define the location of the hole.
Since your boss-extrusion was a smaller diameter than your hole, the feature will be "absorbed" in the hole.
Depending on the complexity of the hole and design intent, you may just skip the Hole Wizard and extrude-cut a circle through the cyclindrical face (sketched on the plane from step 1).
I hear that SWX 2001 allows you to begin the hole wizard by selecting a plane, not just the flat face of a solid, so steps 2 and 3 can soon be omitted.
I hope this is what you were referring to. If not, please clarify and I'll do my best to help you out some more. You can send a sample part file to the email below and I can show you that way also.
--Scott
Interface, Inc.
Scottsdale, AZ 85260
scottw@interfaceforce.com