Thanks for the perspective, I'm entirely new to the space. We're supposed to use ArcGIS. So if this turns out to be the least painful path, I'll have to learn to deal with it...
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.