I don’t know if this idea will work or not. But before you have a system good enough for people to pay for. You could have a system adapted for people to support their friends and relatives in an easy manner. In the example below moving the mouse to the right side border or some corner will show a pop up question area. Pressing this will initiate a chat window. In that you can write your question with text and images. Since we have a lot of free software on Linux. It might be a good idea if the most popular software are supported through this system besides the operating system. I’m thinking GIMP, LibreOffice, OpenShot, Audacity, VirtualBox and so on. If people were then able to improve their productivity in this way maybe they would reward this service.
Thinking about this further. I would think it would be smart if the company or the employer would pay. Even if the questions to the chat support seem to be non work related. A more IT savvy staff is a good thing.