Maybe I'm clumsy, but I find that if roots are young, they can be very fragile. It's really easy to snap them during the process of transplanting them. And if the planting medium is loose (e.g., lots of perlite), the medium can break apart taking roots with it. You can end up with a stick in one hand and roots in the other.
So I like to wait until the roots have aged and toughened just a bit, branching enough to form at least a minimal root ball.