Years ago I used to do a lot of CSG, so when I’m modeling, I think in terms of spheres, cones, boxes, differences, intersections, and unions. As every one knows, or has found out very quickly, Booleans don’t work nearly as well with meshes as they do in CSG.
For some things it seems like you need Booleans. Recently I saw a nice rendering of Bender from Futurama on this site where a Boolean was used to cut his mouth leaving artifacts around the corners. Someone else was using it to drill a little hole in a spray paint nozzle.
In order for me to achieve anything near decent results, I have found that I need to add geometry to line up with where the Boolean will cut. For the example picture below I added ring cuts, parallel to the ground plane, and the results were a little better. I used to use a 32 vertices tube for the base, and 16 for the cut. Auto smoothed it, then added a level one subsurface, and creased the appropriate edges.
Is this a reasonable solution? Or is there a better way to do these sort of cuts?
Left is without the ring cuts, right is with them.