
Is there a simple command that will tell me what "sort" of object the mouse is on?
No signle command, but there are macros SP_IS_RECTANGLE, SP_IS_USE, SP_IS_PATH and so on.
- what "mode" the mouse is in (selector, rectangle, text, etc)
I think there's a function for that in tools-switch.cpp
- what object is under the mouse. (and notice "multiple selections")
The number of selected items is easy to get from SPSelection.
Is there an enum of object types anywhere? At least the sense of object vs stroke?
What do you mean by "object vs stroke"? Maybe a shape (rect, star, etc) vs. arbitrary path?
Also, should the menu be long or deep?
Use your judgement. The menu cannot be too short, Inkscape is a complex program. I think using submenus is OK - after all, this is what people have always done in Sodipodi, and some of them even like it, who'd-a-thought...
For example, if multiple items are selected, the set of boolean operations should be included, but that would make the top-level menu very long. A different way would be to make a separate "boolean" submenu... thoughts?
Yes, booleans in a submenu sounds good to me. But again, I never use that menu, so cannot really judge its usability.
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