Windows 95 -> 98 -> XP -> 7 -> 8 -> OSX -> Arch (1 month) -> Gentoo (1 year) -> VOID (3 years) -> NixOS (4 years) (transitioning to Guix System now)
For reference, this was my editor hopping journey which started during my OSX days since I learned to program during this time: Sublimetext -> vim -> neovim -> emacs