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Wing shows docs, call signature, etc in the Source Assistant tool, available from the Tools menu, and not by hovering the mouse. That continuously updates to show information for the current context, which can include anywhere your caret is in the editor, the current auto-completer item, selection in Project or Source Browser tool, etc.

You can extend Wing Pro in several ways: (1) Add a command in the OS Commands tool (also in Tools menu) and bind that to a key binding in the command's configuration, (2) add functionality with Wing's scripting API and bind that to a key, add it to a menu, or add a toolbar item to invoke it.

And example and documentation of scripting the IDE is here: https://wingware.com/doc/scripting/index

Please don't hesitate to ask if you have questions when writing extensions to Wing.