It is hard to give very specific advice without being able to see the plant (I know, you told us about that). Still, your drooping branches are unlikely to pop back up again. In succulents, droopiness is more likely to be because of insufficient light causing elongate growth than because of lack of turgor. If you water a couple of times and nothing happens, give up on this idea.

Others might disagree, but if you want branches to grow off of lower parts of the stem, my experience suggests that really good light exposure to that part of the plant is necessary (i.e., bright outdoor sunlight or strong artificial lights). Unless you are in the far south it is probably too late for sun until next spring. The most likely scenario, however, is that you remove a lower branch and the plant grows up from the top and the lower branch is not replaced.

On the good side, you can prune at any time. In general it is better to do so when the plant is growing, particularly if you want to root the pruned off parts into new plants. But the main plant should be unaffected unless it is soggy and wet. My sister in law had a nice jade frost-bitten by an early frost a couple of falls ago, and it died back to a 2" stump. It started growing back right away, and is now starting to look like something again by now.

I guess I would think what the plant would look like without any branch in the location of your droopy one. I would keep the plant cool for the winter so that it didn't try to grow very much when light levels are low in winter, and then work it outside in the spring (but not when it's too cool, because you could sunburn it if it's completely dormant). And, I would try to turn pruned off parts into new little plants.

Thanks for your response pasi.
You could be right about the lack of light. I thought that the red edging of the leaves indicated that it had seem some sun but now that I think about it the leaves are much darker than the jades I've seen and most of the mature leaves are about 3" long (which I think is pretty long but I've never seen a Hobbit in person before).
Right now it is suntanning. Right now my plan is to gradually move it to the windowsill, and if things don't improve in 6 weeks let the soil dry out and take a bunch of cuttings.

Hey, Wonder!
You can prune a jade almost any time of year, although Spring and Fall are my personal preferences - especially with these slower growing sports, like 'Hobbit' and 'Gollum,' it's best to utilize the growing season to the fullest. If you take cuttings now, they'll have roots by Spring. And your main jade will show new leaflets.

Jades need sunlight....real sunlight is best. If your jade is inside and it's not right up against a window, it won't be happy. The growth will be long, leggy, droopy, and will not develop woody "bark."

This is what my 'Hobbit' looked like on New Year's, '07 -
{{gwi:571159}}

And here's what it looked like in July, '08 -
{{gwi:571160}}

Josh