That's exactly where I feel I'm at. I'm no tech expert but I'm the guy family calls to help with computer stuff and I know enough to realize I don't like the direction Windows is going. I've gone as far as to install Linux on a single device I use but now I just use that device less cause I can't be bothered to figure it out when I've already got other machines that I've got working just the way I like.

Feel like I've come to a wall that yeah, I could overcome and climb, but this side of the wall is still livable and I'm not even sure the other side will be much better.

Either that, or they use specific tools that they can't or won't replace and which don't work on Linux. Usually it's creative or engineering software. There are usually good, Linux compatible, open source alternatives, but they're not the same as industry standard tools that they need to know how to use and be 100% compatible with. Windows or MacOS is your only safe bet there.

If you're a mere hobbyist and interested in learning new tools it's an entirely different answer. You can try out the windows versions of the alternative software first, then try switching to Linux down the line when see the greener grass.