autorandr VS awesome-sharedtags

could use the postswitch hook provided by autorandr, though this would require letting autorandr manage your display layout as well: https://github.com/phillipberndt/autorandr

autorandr worked great for me for hot plugging when I would frequently use my laptop with two external monitors.

Autorandr does run in the background as it is a daemon. For systemd integration see https://github.com/phillipberndt/autorandr/blob/master/contrib/systemd/autorandr.service

I use autorandr (https://github.com/phillipberndt/autorandr) to load display configurations with a hotkey. I'm 100% sure there is a "better" way of doing so over my setup.

If your using X11, try autorandr. It's a bit clunky for me with the windows moving around after waking up but they eventually find where they're supposed to be... mostly.

I would suggest taking a look at something like autorandr to help dynamically adjust your settings when you connect/disconnect.

There's also autorandr that allows you to save monitor setups and automatically switch between them as you connect/disconnect displays

autorandr (link) (xorg)

No, but you can save settings to script and run on login. Arandr does it with GUI. Autorandr automates and manages multiple setups.

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