I also do programming and am fairly used to the terminal, and I still have a headache when thinking of going back to linux, because even when I want to do something as simple as watching netflix on firefox I had to go through a maze of troubleshooting via the terminal to get the correct packages installed. I can't imagine what someone who isn't tech savvy who tries to switch to linux would do.
The user experience on linux and its distributions just aren't there for the everyday user, and until they are, windows will always be the preferable choice because it actually works. You don't have to end up having a dispute with it on some arbitrary software download because it doesn't quite like it, and have to wrangle through many software alternatives that aren't always available or even anywhere near feature ready because they aren't available on the platform.
The thing with your first statement is there's so many times dealing with software when you are meant to just click 'yes I'm sure' that I've become desensitised to those warnings.
I think of Google Docs now because the inconvenience of not being able to have word on my own system without a price caused me to use the free alternative.
I've done this once or twice myself, and at the moment of accepting the invite I'm absolutely down to do it, but when it gets to the day itself sometimes it's way too hard or I didn't anticipate how it fits in with other events.
But he didn't say "would help" he said "needs". It's quite clear in the interview.