I would like to be able to toggle ToolTips on and off, however being that it's a value in Blender's Preferences I don't see anything register in the Console when I enable or disable it. This makes me think it may not be possible to assign a keyboard shortcut to it. Does anyone know if there's a way? Thanks.
As sambler points out, my answer is overkill for your purposes. However the general question deserves an answer too: How to assign a toggle shortcut to a preference.
Make a new keyboard shortcut or re-appropriate a shortcut you don't use.
UserPreferences -> Input -> Window
If you add a
wm.context_toggle and hit enter you'll get another field called "Context Attributes". It might appear that you can't type into that field but you can. Paste into it:
user_preferences.view.show_tooltips # or user_preferences.view.show_tooltips_python
depending on what you need.