Reply To: Problems with subsurface and intersecting geometry, finding it hard to completely eliminate pinching and distortions, seeking a better workflow or order of operations

I couldn’t seem to let this go and yourNormals comment triggered something. Here’s what I was able to do with Booleans, Subsurf, a couple control edges and Normals (Auto Smooth).  This is set to Shade Smooth. If you subsurf and use control edges on the Boolean object you can get the inside of the cut totally smooth as well. This might be more than you actually need to do for this project, but it might come in handy in the future!