Quality article you have here.
One of the fear of Entrepreneur is fear of selling just like you say. If something needs to be considered, I really think that fear of selling can be eradicate of which you have mentioned some. "Telling someone you already build relationship with or interact with is more easier than selling to a total stranger because you will be free to express yourself." Relationship aspect is very important also. As it will be very difficult to get a stranger convince of your products but when relationship are established, it becomes easier