Many of your specific ideas are excellent and I love your enthusiasm.
Your general approach of getting them interested first, by showing them the good things in free software, is reasonable. It sounds like a great way to get people started. I have followed this approach myself at one point. In fact, if free software required no sacrifices in convenience, then that approach might be good enough.
We want people to come to the free side and to stay on the free side. People have to want to stay here in good weather or bad. If they come here expecting good weather all the time, they will leave when they get some bad weather. They need to come here because it is the ethical thing to do. Then there is a chance they will stay here even if it is inconvenient for them, and even if things don't go smoothly for them.
