[exDM69]

> In fact does X even support monitor hot-plugging?

Yes, it does. It's called XRandR.

Not sure how your desktop system handles it, is there a pretty graphical widget or how you configure it, I don't use a desktop GUI, I set it up with the xrandr command line tool (which is more easily repeatable than a GUI, albeit less discoverable).

> I assume this is because the thing that does the reconnecting is a GUI tool of some sort.

You're probably using network-manager, which is a graphical widget in Gnome (KDE has something similar). There are other methods of setting up Wifi (I use wifi-menu on Arch Linux).