Technology
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It's not learning linux for me; I've worked with it professionally for over a decade at this point and started with old distros on floppy at home (with poor success; it got better once I got gentoo and broadband).
The pain of switching is non-zero, but it's also not high. By this I mean just the process of moving data around, settings, etc.
Finding replacement apps can be annoying.
There are some things that still bother me, though. Certain games still won't work or aren't stable. This impacts some people more than others depending upon the type of game. For me, it's still being gun shy because updates have caused me huge headaches including requiring a reinstall even in fairly recent times. I've had to fix one windows update problem in that same period of years and it did not require a full reinstall.
I have a full-time job, house/yard maintenance, and a small farming business. I require reliability with security (so not updating is not an option) and don't have time to spend diagnosing and solving issues. I also can't not fulfill orders, etc. because of an issue bother from a customer retention standpoint but also because when selling farm goods, those are mostly fresh produce with a limited TTL.
I have 12 months to reassess things, but I'm not liking my current position. It doesn't help that a lot of the software for the Japanese side of things (tax office, accounting, etc.) do not have cloud versions and require Windows to work. I'm not sure if any of those work under WINE or similar at this stage.
Steam has a native Linux client that uses a custom version of Wine called Proton. It handles all the emulator settings for you. All the Steam games I bought in Windows run just fine under Linux. And amost all my older, non-Steam games (like Deus Ex or Giants: Citizen Kabuto) work great under Wine.