grobi VS awesome-sharedtags

grobi (link) (xorg)

I don't know about whether desktop environments support this. I was going to say you may need to write a script for it, but I see https://github.com/fd0/grobi definitely supports it.

I am using an xrandr helper (grobi) to set my screens up when connected. Problem is, my awesomewm config can only handle those changes on start. So I am just restarting awesomewm on screen change.

If you use any tiling layout, they will adjust to a screen size change. However some additional actions should be taken to move your tag structure from one screen to another. I use shared tags to move my tags.

Make Xorg believe that window is visible. For example you can add a fake screen which will show all offscreen windows or at least ones you'd like to capture. On this way you'll face another problem: you can't show the same window twice. Moreover the window may be tagged with tags only on the same screen. It is possible to partially overcome these limitations (see sharedtags for example).

After you figure out your power and screens configuration you'll need to move the tags to other screen once their screen disappeared. It's already implemented in sharedtags module. Even if you're going to implement it yourself you can use the module as a reference.

I have an issue with using charitable / sharedtags and rules, The issue is that when I spawn an application/client that has rules, while the workspace/tag it is supposed to spawn on is visible on another screen but not focused, awesome freezes/crashes.

You can't show the same window on the both screens simultaneously (that's an Xorg limitation). Look at shared tags. This module allows you to move a tag with all clients between screens.

JFYI did you try https://github.com/Drauthius/awesome-sharedtags?

You can have a look at the shared tags modules that implement a way to share tags across multiple screen : https://github.com/Drauthius/awesome-sharedtags