@gmmi
I think some of the people work and in-between stuff is exactly what people need while hosting
And then try and align as much stuff with all the other things that grow from that... slowly level up / people 'accidentality' find their own affinity.
Give people a menu for setting up something and also making it portable / easy to exit if they wish to go elsewhere and without much discomfort.
Having someone hold hand and even being allowed to ask stupid questions really goes a lot quicker sometimes in improving things or getting ideas open, more than people just not doing things or doing it badly. Just asking and get on with it!
So if you're comfortable then I think you can really process and complete people's life...
I think I would look at some of your options and even act as a more of a beginner if you like, as a kind of test conversation theoretically or practically also in testing. For example if I wanted to move an existing blog or yeah consider how I'm doing stuff... maybe move operating systems totally and get regular step by steps by installing onto another machine / usb key or LiveCD or something...