First experimented when Windows 8 took away Aero Glass and other customizations. Committed when I had to fight with Windows 10's twice-yearly feature updates that messed with my settings and wasted space with new programs I didn't ask for. I now keep a separate laptop just to run Windows when I have to.

Distrohopping was mostly confined to my first year using Linux. Deepin (kept crashing) -> UbuntuDDE (went unmaintained) -> Arch Linux -> Debian. Settled on Debian Stable since it just works, I haven't been using bleeding-edge hardware, and I don't like things changing around too often (see my Chicago95 rice).