I have catts that stand up and catts that flop all over. I think they fit better if you want to tie them up, but otherwise I doubt it matters.
The little one should be repotted when it is starting new roots, so they can adjust to the new type of medium. You'll have to make the call if you think the current media is causing root problems. The size of the pot isn't too bad for the size of the plant and I can't tell from the picture what its planted in. If its just moss, then dampen it when it is getting pretty dry and don't get it water logged and it should be ok for a while (if the roots are ok now).