Another interesting question is: What OS did you use the most (total time since 1985).
To me this would be 1.3. I started with Kick&WB 1.2, but WB1.3 was already out when I got my RAM expansion. I didn´t upgrade to 2.04 until 1992 which makes it 5 years of daily usage for WB1.3. In 1995 I got my first LinuxPC and didn´t boot into Workbench that often anymore. So only 3 years for 2.04, 2.1 and 3.1 combined.
I am now in my second year of AmigaOS 4.1 and I hope it will be good for another three years. ;-)