Oh don't worry about not having cantering confidence! Its taken me five years of horse ownership and several small attempts before I finally got my mojo enough to canter without getting in a fuffle about it all! I don't have a great seat, and its not elegant to watch, but at least I'm getting back into practice with it. Don't feel pressured tho - just do little bits and build on that. If you're going to have lessons then make sure you express any fear about it to your instructor - you don't want to be pushed too much and scare yourself (which is what happened to me a long time ago). A good teacher will know how much work in canter to give you. Good luck!
). She decided that she would make a deal with herself. She bought one of those straps for the front of the saddle (fits d-ring to d-ring) and said she would use it for 15 ride outs on her horse. It was a security blanket for her to ride where she had come off. She also wanted it incase she tensed up in the saddle and became unseated or unbalanced. It worked and after 15 rides she took it off. This might be an idea but set a limit as you don't want to become dependant on a security blanket. We ride out all the time now and theres no stopping her and she loves it. Good luck but try not to focus to much on it, it will just happen when your ready, and he sounds like a horse that would look after you 
Once you do it like you said that will be it. But don't beat yourself up if you don't. Ive been getting Abby back into work after injury since February and we have had nothing near a canter 
But i know we will its just when shes ready. It will happen and im sure your riding is quite satisfactory, you stay on and enjoy it, there is not much more too it in my eyes. Keep us updated and enjoy it, either walk or gallop! 