Once a cutting has rooted and you accidentally break off some roots in repotting, they generally regenerate their roots faster than if you were starting a new cutting. At least that has been my experience.

Something you may want to try is dig small holes towards the edge of the pot (drill size holes) and drop a few pellets of time released fertilizer in them. The roots will grow toward the fertilizer and you should get a more spread out root system.

I don't know if you tried this, but when I repot a plant, unless it is too big, I place my hand at the base of the plant with two fingers around each stem, turn the pot upides down, and give it a few gentle knocks on a hard surface. The plant usually just slips out of the plant. If the soil falls off, it doesn't damage the roots as much as it would if you pull on it to take it out of the pot.