I am by no means an expert but I know some things. I share a lot of your questions too.
5) What are GTPlayground "Bindings" and in which case does the "Refresh" > make sense? > The bindings show which variables have been defined in the Playground's workspace and which object are they linked to. Variables are created when you execute code such as: *number := 24.* Have you executed code like below: *| text |* *text := 'Hello ninjas'.* This wouldn't generate a binding. To know what's binded is important so you know if you are leaking objects or if you have unwittingly declared a variable and you script is working oddly.