In their (possible) defence, stepping outside the the narrow ESRI path of the way you're supposed to do things makes your life a massive pain. I used to work for a company that (among other things) developed tools for clients on top of ArcGIS Online. And I've had many calls where a client asks for a small and very reasonable change, and I embarrassingly have to explain that that is not the 'approved' way doing things in ArcGIS Online, so trying to make that change will essentially require us to rewrite a whole lot of components more or less from scratch and might no even be possible.
I've spent a large number of hours trying to fight ESRI software, lost more fights than I've won and even my victories have mostly been pyrrhic.
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.
I've spent a large number of hours trying to fight ESRI software, lost more fights than I've won and even my victories have mostly been pyrrhic.