People that do these sorts of remote work via GUIs exist. But yes, the switch is likely pretty obvious to them. I for one used to do it with Minecraft server stuff, I had FileZilla; Dolphin pretty much replaced that instantly for me. MUCH later, scripts replaced Dolphin.

They exist, but they already know that Linux is an option. It's not a selling point, it's a bit of an echo chamber about how it's possible to do the things you already know every OS can do. If you're messing with those things you've been in a million tutorials with segments on how to do stuff in Win/MacOS/Linux over the years.

Is it though? They'd face the same issues switching to MacOS. There's no point in lying that some of their favorite programs may not work. I still miss Paint.net though GIMP has grown on me a lot.

If GIMP has grown on you a lot you probably should check with a doctor about that. Because ew.

I think it is. The scale to which you'll have to swap software solutions is way larger in Linux, which is why nobody is writing the same advice for Windows or Mac marketing. I'd argue Mac-to-Windows will lose you more options, but either way the expectation is that the software will be there for you or that you'll have a better alternative that is an actual selling point. "Come over and see if you can find a viable alternative to all your work software" is a huge dealbreaker.

Nobody is going to leave their old Windows files on their OS drive AND install Linux unless their goal is to dual boot (and that's clearly not who this is for).

Isn't it, though? I mean, I get why you wouldn't float that option when you're trying to push people to move over entirely, but... that's definitely an option.

The entire file system needs to be replaced in the process of installing Linux, so there's no "somebody should find a better solution to this." The only way to do it would be to relocate and resize partitions as files are copied ... and that's incredibly dangerous. Not to mention attempting to guess what files are important to the Windows user has a high probability to fail.

Well, yeah, but you're describing the problem, not a solution. Let's say that there is no technical solution to preserve a data drive across OSs (there is, but hey). That's an inconvenience, at best, a major problem at worst. In a world where Windows will update you without messing with your partitions and even a clean install will preserve your separate data drives (which Windows has encouraged splitting from the boot drives for a while), this is a reason why you'd be discouraged to take on the more finicky, annoying process of moving everything over to Linux. Especially if you don't know if you're going to like it and may have to move everything back.

People should update software (at least when there's a security related issue) ... for the exact same reason they should ditch Windows 10. However, as you said "Having to explain to people that their perfectly working computer is actually not working despite all available evidence is a bit of an issue."

Yeah, I've always been torn about Windows' approach to updates because of this. I do want automatic updates. I don't want to have to remember to manually check for and fire off updates. Especially when the longer you wait the more of a gamble it becomes that something will have broken after you're done.

This became a meme on Windows because their early implementations of Windows update were insanely blunt and annoying. Nobody wants their computer to reset in the middle of a presentation or a game. I'd say that an automated reminder to update or an update scheduler are not inherently a bad thing, though. For big sysadmins that will only update what's strictly necessary you want the option of manual updates, but for desktop users who typically will want to be on latest for everything? Just letting their computers update overnight or on every reboot isn't the worst idea ever.