Not exactly the same, but something that got me a couple weird looks at the time was paying almost $100 for RedHat Linux (6.1, Cartman) in 1999. I'd wanted to use Linux for a couple years (I thought it looked hacker-ish and had watched _The Matrix_ in theaters not long before that). But my PC didn't have a CD writer. My 4.3GB HD didn't have enough free space to download the ISOs. And I didn't have internet access. So…
The first time I called with a question, the support agent suggested that I maybe check the man pages? At this point, I’m an unreformed Windows user and I’m just trying to set up my system, I have no idea what a man page is! As I recall, I was just trying to get into the GUI - not sure why they couldn’t have just said “startx”.
Second time I called with a question (by this point, I had learned enough to know to ask the question “how do I create a non-root user account?”), they suggested I hop onto their IRC channel and ask the community. I logged on to IRC and … promptly got booted for being logged into my local system as root. Strike 2, I was out. A few years after that, OS X because semi-usable (10.2?) and I didn’t have much use for Linux for the next decade and a half.
Now I run a couple server-ish boxes on Debian and quite like it - there’s not a whole lot I know how to do, but in those narrow domains that I semi-understand, it works very well for me. But even with as much progress as it has actually made in the last few years, I’m not sure the year of Linux on the desktop is imminent for me any time soon.