This year, so far, I've moved two older family members over from windows 10 onto Linux. I opted for an ubuntu based distro as I'm familiar enough to troubleshoot it, even remotely.
The first was a laptop, about 10 years old; windows was unusably slow. Luckily, the transition was smooth, Linux Mint took first attempt and no issues were had, everything worked out of the box except swipe scrolling - a quick tutorial sorted that out (terminal intervention was needed). 4 hours total setup (including a pile of desktop shortcuts), dual boot just in case she had issues.
The second was an older machine, a desktop, Frankensteined out of old parts (oldest being the motherboard at 15 years old). It ran windows 10 without a single hitch or slowdown.
2 days to get it "running", I had to repair grub to get the damn thing to boot after an install finally took. In the end I had to go with lubuntu with a manual cinnamon install because I hit my 4th mint install attempt and got a strong case of the"fuck thats". At the end I have a machine that has ghost headphones flickering into existence giving choppy sound that is pretty unusable. There is also horrific graphical glitches when booting (harmless, but I crapped a brick when I first saw it) - though I suspect this is just the fact there is an elderly Nvidia card in there.
A lot of time spent in terminal was unable to even identify what was happening - a first for me! My money is on a bios update, but yeah, not fun on old boards.
All in all, two very different experiences. It's not a warning against Linux (make the change now while the support is there!), just a warning that the road isn't always smooth. The bumps can come in odd places - you'd think the laptop would be the tricky one but nope, desktop rig was the worst.
Good luck out there with the change folks!
A genuinely heart warming story that deals with strong themes of love and friendship in a way that made a genuine impact?
Undertale.