I plug my 2021 16" into a dock nightly and while I do have to reboot once in awhile to "reset" things (which takes literally ~8 seconds depending on what I have open) due to this platform being relatively new for desktop use, I plug in and 99.9% of the time my displays just work. And I don't even open the laptop, just take it out of my bag and drop it into my dock and plug in one cable.
Windows 10 is simultaneously the best and shittiest Windows ever. I like some of what they've done, but lots of what they're removing is power user features that are legitimately useful and have no Metro alternative, and often just drop you into a legacy applet anyway. We have lots of speedy Lenovo Tiny machines with Win10 that are good except that Windows routinely has an "error" that coincidentally defaults the PDF reader and browser to Edge for no reason. It's all the little antagonistic shit like that, or driver bullshit, or constant nagging about all kinds of random minutae that confuses end users and makes life a living death by a thousand cuts. Windows 11 looks to be even worse. I get they need to ditch the legacy code. If they were replacing it with something legitimately useful, I'd be more diplomatic.
As it is, the sins that Apple commits are more "ugh, that's annoying but at least I don't have to deal with this at crisis time", vs Windows consistently fucking up crucial things that require time or research, like nuking printing in such a way that I have to dig through endless forum posts to find the single registry or GPedit hack to get it working again, or the constant, CONSTANT stream of useless updates that you can't disable. I thought I'd be clever and create a stripped Win10 image to use on our new Windows machines going out, disabling automatic updates, and removing stuff that people in an office setting (I work for a school district, these are meant to be used for secretaries and custodians) will NEVER use. Stuff like XBox integration, gaming, OneDrive, baked in Office install, etc. I then found out six months later when a few of them just dropped like flies overnight for no discernible reason, that doing this breaks Windows Update in such a way that a new update will still download, attempt to run, and nuke the install to the point that no amount of fucking with it will revive it, and you have to just reinstall from scratch and copy data from Windows.old. Yeah, more fool me for messing with the install, but at this point Windows is such a dog's breakfast of old and new code haphazardly duct-taped together that it's infuriating to use and even more infuriating to support.
Not to mention that Windows somehow has this ridiculous bug where the mouse pointer will jump sideways 25 pixels or so for no reason every dozen clicks or so. There is no rhyme or reason to why this happens, and it seems to occur regardless of drivers or hardware. Every model of laptop I've ever used with Windows 10+ has this bug, it has never been fixed, I've seen random forum postings about it but no fixes, and every time it happens I am reminded why I use a Mac.
As it is, MacOS is robust, consistent and for the most part gets out of my way and lets me work, and if I need Windows, I have Parallels. Apple does annoying, antagonizing shit once in awhile, but the MacBook Airs and iPads we deploy in our district are relatively trouble free and durable outside of some aspects of using non-Pro model iPads in a laptop role, and the inevitable Apple locking down of features that would make life in an educational environment so, so much better. But there are no showstoppers that make me want to break the thing in half over my knee.