I have Linux on all my servers, was an early (very minor) dev on pre-1 kernel and generally love it.
The desktop is a walking nightmare. Something continuously does not work: multiple screens, waking up from sleep etc.
I really would like to move (we use Outlook but I am even ready to go for OWA) but Windows is considerably better on laptops.
Again, I love Linux and have managed literally thousands of them since 1994.
In all seriousness, until about a year ago when I got a discount on a Macbook and changed to that, I had been running Linux for about a decade across different laptops, and feel that since ~2017 the desktop experience has improved substantially. I bought a new laptop in 2017, installed Ubuntu on it...and that was it. I spent exactly zero minutes installing drivers or mucking with configurations, multiple monitors with HDMI audio worked out of the box, and "going to sleep upon the lid closing" just worked. Granted, I'm a bit of a Linux veteran at this so maybe there were a lot of things I was tweaking that I just don't remember since I do them so often, but I do not think that was the case, since I got my wife (who is not a software engineer) using Ubuntu as well for awhile.
I think part of what made it better was using AMD hardware for everything. The drivers are just included with the kernel, and they work great out of the box, at least for me.
I realize that telling everyone to shop for a computer based on the drivers that will be available isn't exactly a great sales pitch for Linux for the average consumer, but I suspect if you frequent HN you probably have a reasonable ability to differentiate video cards and whatnot.
Windows is always getting worse, too, but still basically works on all hardware. I've been thinking of switching away, given how bad Windows 11 looks to be and how irritating Windows 10 has been. But then, Windows XP, Vista and others were also known to be terrible but still mostly worked.
On balance, I'd say that Windows is likely to continue a user-hostile decline but still mostly work and Linux on Desktop is likely to always have a lot of effort involved if you want everything to work well. But there's probably no point at which Linux will work well on all hardware or Windows will be less usable by default.
Yep, no question here. While Linux compatibility has gotten a lot better in recent years, you're definitely rolling the dice a bit in driver-land if you don't research beforehand.
That said, since pretty much every big distro is free, it's not necessarily a bad idea to just download it and try it out, at least with a Live USB Ubuntu image or something. If it works out of the box, then maybe you should install it, and if it doesn't, just unplug the flash drive and restart the computer and stick with Windows. It's entirely possible (and even likely these days) that it will Just Work (tm), and that might influence your decision in switching.
> But there's probably no point at which Linux will work well on all hardware
Yes and no; I think Linux tends to do exceptionally well on older hardware. I've been able to breath life into decade-old computers by just installing Linux Mint with MATE desktop [1], and generally by the time a computer is designated as "old", drivers on Linux are often better than they are on Windows, and due to how stupidly customizable Linux has become, you can get extremely lightweight desktops that require basically nothing to run (e.g. LXDE, MATE).
On newer hardware? Eh, as I said, you're rolling the dice a bit. Generally if you stick with AMD hardware, you are fine, as I said, but that's by no means guaranteed, and to me getting WiFi to work out of the box is the scariest thing, since if you cannot get connected to the internet, it's difficult to fix any of the problems.
[1] I did this for my grandmother who is still running an old AMD64 single-core computer. All she uses it for is browsing the web and checking email (not even YouTube) and she refuses to buy a new computer. Linux Mint has been a godsend.