Thanks for working with me on this, Yanitch. I appreciate you taking the time to help me hammer this one out. Not exactly sure if this will help, but, here's a bunch of rambling :
Here's what I found with using the DirectX test harness (I can't use Notepad for testing this, since it behaves a little differently than a DirectX game): The, 'Numpad Enter' key, when pressed (hardware keyboard) results in a Keys.Enter value. Pressing the enter key in the alpha area results in the same registered key.
The same goes for the Delete key in the center cluster (the one up there by home/end/insert/etc). If I press it, the DirectX test harness indicates Keys.Delete. If I hold down shift and press the, '.' key in the numeric pad, I get the same result.
Now, having gone through this, I can see how the VoiceAttack UI can be a little bit confusing. It's a case where the UI matches what is going on underneath too closely. For instance, there is no scan code for the, '$' key, so, in VoiceAttack, you can't specify this as a key. You would have to do a, 'Shift + 4' (the alpha 4). Likewise, if you are wanting to do a Right Arrow from the numeric keypad, you do not have that as an option. You have to do a, 'Shift + Numpad6', or, hit the right arrow key in the center cluster. Short of providing a graphical representation of a keyboard, I'm not sure how to implement this properly. I could possibly pop up a box when in, 'DirectX mode' and a numpad key is pressed...