Running Debian since 1999, it was a pretty steep learning curve. 486DX4, 128Mb RAM, 1 boot floppy and 13 other floppies got me a black screen with a flashing cursor. Felt like being back in 1982. Turns out it was the only OS with integrity. It was able to connect to a dial-up server, all command-line.
Three nights of downloading on a 56K modem through the phone system at work (data was expensive back then) and weeks of setting up config-files and selecting apps in ASCII-graphics interfaces, supported by the gracious geeks on the debian mailing-list. The joy and pride of a working GUI.
Later, I built a fanless PentiumII. Never switched it off in a year. That was outrageous in 2001...
These days, it's a whole other deal. I've forgotten most of the bash I learned back then. Install is a 45min deal, everything just works. And I've also almost forgotten the tedium of Windows, the nagging, the wait for updates, the virus-scare. Linux updates while I'm doing other stuff, it has memory integrity, never crashes, is immune to vira and other nasties.
Using the last good Thinkpads: X220 as daily runner (2011) and a luggable W540 for the bigger screen. Tried a few newer models: flimsy screens, shoddy build, keyboards fall apart. But that's a whole other rant...
Cheers, happy New Year!