I switched a lot earlier - 14 years ago, and maybe I’ve just been lucky but I’ve never had to worry about there not being enough space on a drive for an OS update, or any of the other woes you mentioned.
As for “troubleshooting their computers” - that is something I have to do with my work (windows) computer, not with my own Linux system.
A lot of people get hung up on perceived limitations of native applications. For example GIMP isn’t an exact replacement for Photoshop, nor is it intended to be, but I’ve yet to find anything I can’t do in GIMP that I actually want to do. Sure - PS proponents can come up with a list of stuff that GIMP can’t do, but none of them are fatal errors as far as I’m concerned.
Likewise LibreOffice isn’t MS Office … thank goodness. I have to use MS at work and Office 2016 is downright horrible.
My current computer came with Windows 8, that failed to shut down properly twice in the first 3 days. It’s still on there - I never got around to removing it but it’s never used.
Linux is probably not for everyone, but it may well be the better choice for most people. One that’s certainly worth trying. For newbies I’d suggest Mint, Elementary, or Lite.