I've been considering the multi-window approach, to leverage the system's taskbar, which is natural to use, but I don't know if I'd open more than 2-3 windows,

I've been considering the multi-window approach, to leverage the system's taskbar, which is natural to use, but I don't know if I'd open more than 2-3 windows, since it would fill the space quickly (unless I use a taskbar that groups items).