I was always wondering if it is possible to sculpt holes and arches with dyntopo (without needing to do booleans), and why it is not implemented in blender yet.
I did some research and found that there is not really many softwares which allow such manipulation. Only one sculp tool which allow me to make holes without boolean and bridge is webgl sculpt tool
Author of this tool gave us all sources in github
Maybe it is possible to implement some of his features in blender?