It has worked automaticlly for me for the last decade using different distros and the *BSDs. I do remember all that trouble though when I started experimenting with Linux/BSD in the early 2000s.
There are 2 things that cause this. Not having a driver installed and having it fall back to something which doesn't support the correct resolution or in fact bad cables.
Most user installs will not encounter either problem. New amd has great support out of the box without installing anything and many distros support installing closed source nvidia or will work well enough for non gaming applications with the open source drivers.
Please note that challenges aren't a result of X they are specifically the result of specific manufacturers drivers. Some of which have been more challenging in the past. For improvements on such in the future look to the manufacturers and support the ones that provide the optimal experience.
Please note issues where users can't set the correct resolution for their hardware ALSO occurs on windows 10.
How many distros will install e.g. the proprietary (i.e. covering most recent hardware) NVidia drivers out of the box? If I remember correctly, Ubuntu only just now started doing this.
You do need them if you want to use recent hardware, or get decent performance, or have working power management. From casual user's perspective, if this kind of stuff is not working properly, it's not really "set up".
Good point. Historically AMD/ATI didn't provide official support for hardware for anywhere near as long as Nvidia and the open source gpu driver didn't provide near the same performance. For example devices could be available as new retail units one year and unsupported less than 3 years later.
To contrast that nvidia generally provided support for a decade. For example the latest release only days ago supports hardware as old as 2012 legacy drivers support hardware as old as 2003.
This is why I have bought nvidia hardware despite other issues however it looks like AMD open source support will be better going forward. This doesn't help anyone with old hardware.