If it were me, I would repot the second one because it needs it, and the first one to put it in a medium and pot I am comfortable with. But if the first one is drying quickly enough I might just put it down in a clay pot for stability and wait to repot until it really needs it or I'm nervous about something in the roots. On the other hand, the sooner you repot it the easier it will be to remove the moss from the nooks and crannies of the roots.