I don't transplant autos, and I almost always stick to plastic pots like you do until final homes in cloth for photos, but for the times I have had to move plants from cloth to cloth, I do pull the bags down around a bucket (as seen here). But whether you do it my way or the velcro way, you will still be tearing off the air-pruned roots even with a velcro pot.
But those roots are already dead from air pruning, so there's not harm to the living roots.
But those roots are already dead from air pruning, so there's not harm to the living roots.