What do you mean by issue? After a couple of xrandr invocations to configure them, which could be automated by some GUI app if I were so inclined, I've never seen external monitors have issues on either of my Linux laptops.
Requiring an xrandr invocation equals to having issues. Perhaps it's a small problem, perhaps it's a very easy problem, but it definitely is a problem.
Not having issues means that you arrive at the hardware (which you may have never seen, e.g. at a customer's site), plug the wires, and it works immediately.
More importantly, not having issues means that you can rely on being able to just plug the wires and have it work, and that you don't have a risk of being unable to make it work immediately even if you forget the right invocations and are offline and can't look them up.
How does it work immediately? How does it know of I want to clone or extend the display? If I extend, do I want the same resolution on both screens, or different? You'll have to set that somehow, and whether it's a GUI or a CLI tool doesn't matter.
Forgetting the invocations aren't really an issue anymore either, my shell (zsh) has autocompletion of xrandr outputs, modes and resolutions.
There are plenty of tools to automate that. arandr is a very simple and powerful tool to arrange monitors with a GUI. Gnome has its own, much simpler, monitor configuration dialog. My system defaults to extending to the right, by the way, because that's generally what I want when connecting a projector.
None of this is new, and the whole point of this discussion is that Linux desktops are much better than they were ten years ago. It is that old state that many folks have in mind when criticising Linux distros' usability. It's just not a very interesting discussion to have.
And the thing I think you're hearing is that "progress" should not equate to "good enough." Doing a sensible and even helpful thing by default is part of user friendliness.
On my Thinkpad's X200 (VGA) and X220 (VGA, DisplayPort), plugging in external monitors has always Just Worked. I've been running Xubuntu on them for about 5 years.
It even worked on the first try from the X220's DisplayPort through a DP-to-HDMI-cable onto a TV.
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I've never had to use xrandr or any command line tool to select displays – on Xubuntu, there's this little graphical dialogue: http://netupd8.com/w8img2/xfce-mini-displays.png that pops up (or you can force it to show by hitting that key on the Thinkpad keyboard with the picture of an external display).
OTOH, I did just a month ago for the first time actually use xrandr, but this time it was because I wanted to write a script that set my windows and monitors up "just right" for how I like it when I'm at the office. I love how easy Linux makes it to do that stuff when I find I do want something automated.
