ArcGIS the desktop tool, or ArcGIS Online? The desktop tool at least has a pretty complete (but pretty annoying) python API so that if/when you have to, you can

ArcGIS the desktop tool, or ArcGIS Online? The desktop tool at least has a pretty complete (but pretty annoying) python API so that if/when you have to, you can circumvent the GUI and automate almost everything. ArcGIS Online is unfortunately extremely inflexible, and things that should be easy are often impossible.