So new to Blender but semi-versed in MAX so sorry if my wordings a little off. I have a weird shading issue, I have this smoothing issue visible in the screen capture, I've tried using the smooth function in the edit>shading menu, I've also tried flipping normal and neither change anything. My modifiers are, subdivision surface and mirror modifiers. Any tips would be greatly appreciated.
There might be few point that you want to know:
You don't get enough subdivision times, usually not going further then 2~3 times. Ctrl1~0 within object mode can set sub-modifier.
Your mask (I guest?) topologies are not suitable for subdivide, it has some holes with special case that blender nowadays can not resolve well. See the reference: Subdivide
The smooth shading AFAICT use Gouraud Shading in the view-port fast rendering. There is fake normal in the calculating pipeline, you might confused that by another common shading: Phong Shading.