> They should make a Snow Leopard-like release and clean out their bug tracker.

We actually had a Snow Leopard-like release just two years ago: High Sierra. It had some new features—as did Snow Leopard—but not many. (Lest we forget, Snow Leopard introduced Dock Exposé and Exchange support, just to name two.)

And High Sierra is hands-down the best version of macOS since Mavericks. But afterwards, things regressed pretty quickly.

The real problem here is the annual release cycle. The entire concept of a transitional release is misguided. If it's transitional, keep it internal to Apple until it's ready, and let Mojave live out another year in the meantime.

This isn’t something I’ve encountered and I dock to three different desk setups most days. It’s typically good enough that it remembers the correct layout for multiple of the same type of monitor once configured. Is your monitor sending the serial number correctly?

It has happened on several different monitors and MacBooks, even putting it to sleep and waking it can sometimes switch them, so I have to go into System Preferences and drag 'em around.

This just started happening to me on Mojave, after I messed around with installing some third party USB managers to try to get my new keyboard and mouse to behave. Deleted the managers and returned the hardware, but some lingering issue crippled my multi-monitor setup. It’s particularly bad because I use one horizontal one vertical.

While I don’t have that particular issue, I have other issues related to external screens, with 10.14 and 2018 MBP: I usually run the laptop with closed lid and an external screen at work and at home; and use it in “laptop mode” during my commute. Now, sometimes (once a week?) when I plug it into the external screen, it just won’t wake up, unless I open the lid, and then it still won’t recognize the external screen. Have not yet found out a reliable way to resolve this, but I usually manage with turning the monitor off and on again and/or unplugging/replugging it, possibly a couple times each.

Much worse is that sometimes (once a month?) during this process macOS completely messed up all my open windows: they are all resized to a tiny size. And I have dozens or hundred of them open. This is horribly annoying, and didn’t happen to me before (in 10.11; I skipped 10.12 and 10.13, for reasons similar to the OP. Before that, I went from 10.8 to 10.11; before that, I never missed a release, often was running beta of the OS etc.; but starting with 10.9, too many issues made this undesirable).

I dread switching to 10.15; unfortunately, I will get a new MBP 16” from work, which normally I’d relish, except that there seems to be no way to use it with anything but 10.15. I’ll see if I can delay it until 10.16 is out and will pray that they started to prioritize bug fixes again, but I have little hope that’ll actually happen.

> I have other issues related to external screens, with 10.14 and 2018 MBP: I usually run the laptop with closed lid and an external screen at work and at home; and use it in “laptop mode” during my commute. Now, sometimes (once a week?) when I plug it into the external screen, it just won’t wake up, unless I open the lid, and then it still won’t recognize the external screen. Have not yet found out a reliable way to resolve this, but I usually manage with turning the monitor off and on again and/or unplugging/replugging it, possibly a couple times each.

I've previously had these problems, and they were made dramatically worse on Catalina. Each monitor has about 50% chance of correctly loading in, on what used to be 90%. My USB mouse (which is plugged in to the displayport monitor) also loads the incorrect drivers until I unplug and replug it.

Ah, I’ve never tried in clamshell mode - long harboured fear of the thermal envelope from the PowerBook days.

I think I heard someone complaining about this when docking to two identical displays (with identical model names in display settings).

I have two identical setups, both with two 27 monitors and to make it worse one is horizontal and one vertical. Most of the time when i go to the other desk the monitors switch and I have to reset the orientation in display preferences. I have been fighting this for two years. Reset everything apple has told me to and no fix at all. Total PIA.

Tried 3rd party app "SwitchResX"?

It's not the resolution it's the orientation that keeps getting flipped.

--- Well I take that back. It's been updated since last i used it a few years ago. There is display orientation savings now. It might now solve the problem, but it sure looks to make the fix much easier and faster. Trying it now. Thanks

Same issue for dual display setup, my workaround is to label the cables and make damn sure I plug them in the same order and same port every time. If I do it wrong I’ve to do the display settings and rotate both screens routine..

Another option is to use the left side ports at work and the right side at home.

Ports works SOMETIMES but since all 4 monitors are identical i still see confusion. I may try the left/right though. Currently all cables are hidden so i'll have to redo some to pull that off.

I commonly do this (hot desking) and don’t have the issue.

I don't get monitors switching, but the apps don't return to their position when I switch from docked to mobile which is a pain.