Maybe one user friendly way from a scripters point of view would be an implementation of a scripting based dockable user panel which accepts WinForms (or ETO forms) in the future. So instead of choosing
Rhino.RhinoApp.MainWindow() as the parent when showing a form like this:
It could be shown using such a dedicated UserPanel as the parent window of a form made in python. From the RhinoCommon helfile i´ve gathered that the registration and opening of the panel could technically be done via python. I´ve no idea how much work is involved to actually accomplish that without compilation but would accept any way to do it without using VS.