Tarev, I have not repotted any plants since the cuttings were planted in 2009. Unless the plant has been knocked over, I don't add any soil either.
You're so lucky to be able to leave your plants outside all year. I read somewhere, when I first started growing cuttings that they're okay with temps down to 35 degrees, of course the growth slows, but no freezing temps allowed. I understand that they do want some colder temps to help the bloom cycle the next year.