This is probably a "patches welcome" thing, but what would be nice is a way to have a dynamic configuration based on the currently connected monitors. It'd be good to be able to match whether a monitor is connected at a specific port, whether a specific monitor (by name or serial or whatever) is connected, and if a specific monitor is connected to a specific port.
People, you can discuss and design your hearts out how monitor configuration should work. However, here on phoronix forums, all that brainwork will be wasted.
If you want to make a difference, write a tentative patch, and send it to the mailing list. Then you could actually get noticed and given feedback.
Also remember, that Weston with the current desktop-shell client is a little like the plain X server with twm. It is not a fully integrated seamless end user experience, and I don't think it ever will be. All that desktop user-friendlyness and integration will come from the big desktop environments like Gnome, KDE, Xfce, and others. If you want to promote user friendly desktops, go help those DE projects to support Wayland.
The Wayland project, or Weston, are not aiming to create yet another desktop environment for end users. They are creating the plumbing, the infrastructure, the underlying engines, on top of which the existing DEs can move on to.
We have Weston and the related bits only because we need something simple to develop and test on, that is completely under our own control.