I still haven’t seen a windows app that will check all hardware and software and give a pain scale rating on what switching would involve.

You can just use a liveboot Linux image on a USB key drive and find out whether there are any issues.

Here's Debian's liveboot images (which they apparently call "live install"):

https://www.debian.org/CD/live/

I imagine that most distros probably have a liveboot image, though I haven't gone looking.

USB drives are maybe slower than your internal SSD drive, but for rescue work or just seeing whether your hardware works, should be fine.

I would expect everything that you listed there to work. The only thing I haven't heard of on there is that dygma keyboard, and looking at their website, if this is the keyboard in question:

https://dygma.com/pages/dygma-raise-2#section-faq

Is the software compatible with macOS and Linux?

Yes, our configurator software is compatible with macOS, Linux and even Windows.

I mean, I dunno if Logitech puts out trackball software for Linux, but if what you want is macro software or configurable acceleration curves or something, there's open-source stuff not tied to that particular piece of hardware. And the Steam Deck is running Linux itself.

There's gonna be a familiarization cost associated with changing an OS. Like, your workflow is gonna change, and there are gonna be things that you know how to do now that you aren't gonna know how to do in a new environment. But I think that that's likely going to be the larger impact, rather than "can I use hardware?"

EDIT: Oh, it sounds like the reason that they call it "live install" rather than "liveboot" is because you can use the same image to both just use Linux directly, and can run the installer off the image too.