From my experience with cacti and succulents that I have, the roots grow very shallow, so consider potting them in smaller containers. As to being pot bound, it takes awhile before the roots fill up, so it is hardly a problem. The main thing to really consider is to plant them in fast, well draining soil.
The jade plants will grow for a long time in its present container. I have a jade plant given to me by aunt and I have potted it in its container since late 2009 and it is happy in it. I notice that the trunk of the plant really gets quite big and quite happy staying there. The jade plant she gave me is a mature older plant, so I have to plant it in a bigger container in consideration of the existing root mass it already has.
Hmm on that photo of yours with a bug..that bug looks like a mealy bug..cotton swab with alchol to remove it. They suck the juice of your plants.
This is the trunk of my jade plant..see how the trunk has grown wide, being a succulent it stores water there and on its leaves, so it really can forego watering for awhile. At times I give it one very heavy watering once a month. By heavy watering, soaking the soil/root area very well, till water runs out from under, then leaving it alone.
