I have been using windows since version 95. I even liked the Millennium version, that was most hated before Vista. I tried Linux several times, but Windows just always worked and Linux usually had always some issues(mostly drivers, lack of good programs and no gaming). But now, after more than two decades, I am certain Windows 10 is my last Windows. Nothing lasts for ever, not even Microsoft's domination on personal…
If you’re this engaged already I’d just make the jump. Be part of the future you want to have rather than watching from the sidelines.
Biggest pain point actually are not programs, but the need to format all hard drives to some linux file system. I cannot just replace windows with linux and that is it. No, I have to migrate all my data somehow to reformat all my drives and then move the data back. That was always huge pain in the ass.