[pixelface]

you've touched on the problem and the solution - number of people using it. for people who were children in the early 2000s it's a distant memory now but adults used to be generally bad with computers and windows was just as much wizardry as anything. be the linux userbase you want to see in the world and help others when they want to join just like the 10 year olds of 2003 handheld parents through computer use. there's never going to be a magic solution, there just needs to be a sufficient number of people using it so that your outlined issue of proximal support gets better.

ubuntu (and i'm sure others) are in a great state for casual users already -- i've handed multiple family members an ubuntu machine with no more instruction than "use it like any other computer, don't be scared by the icons looking a little different" with great success. for the increasing number of people who do almost all of their work in a word processor and a browser exclusively, it's a complete solution with almost zero hassle.