I watered my plants today. Still having winter like weather, I'm watering about every other week. 2 of the ones pictured have rotted. No idea what caused it. The trunks were a mushy mess, but the roots still looked good. They seemed fine the last time I watered them.

Hi Leah, The black spots look like scale insects to me...I would buy some insecticidal soap and give your plants a thorough soaking. The brown spots look like normal wear n tear from the outdoors...I wouldn't sweat it. I have seen similar spots on jades that I have overwatered...the rot manifests as dropping leaves and sections on leaves rotting and turning brown. However my spots had more regular, smooth edges. If you're concerned then you can repot in a well-draining mix in a well-draining pot. I prefer terra cotta because I tend to overwater. Great looking plants!

Ashley You won't loose jade from cutting-pruning-chopping-whacking...:) As long as it is not overwatered = kept too wet after cutting. Your plants are looking quite good but could look even better. Etiolation is more visible on your second plant: the sets of leaves are too far apart. Plant keeps stretching in search of more light; this could be solved only by keeping it in more. Outside will be much better. I also think the soil may be more water retaining than it should, there are lots of 'salts' deposits on inside of the pot. When you water, soil likely stays wet for too long, and deposits build up. First, repot into better draining mix. If you are afraid of pruning, maybe try with one of the plants first: cut where desired. Use sharp knife or blade. Let cut off part to callus - scab over, by leaving it out of direct sun until the cut ends starts getting dry. That may be few hours or even few days. Plant will live, there is lots of moisture stored in trunks and leaves. After callusing, this pruned off piece should be potted into well draining mix. Do not water until roots start growing: no roots - no water. Once they start growing, there is usually some new growth appearing. It could take couple of weeks or longer. Part with roots should stay potted and will start branching where it was cut.

Assuming you are in the Northern Hemisphere (fall going in to winter), I would not "cut at the red line" at this time. The plant will be going dormant now, but in the spring you should be fine assuming you allow the base to callous before replanting (and don't overwater), as you must have done when you got the cutting in California. As for the other pruning, it looks like you will mostly be leaving bare stumps. I always cut back to where there is something else sprouting. I would suggest you wait until spring to do that as well. Of course, you know all those cuttings you make can be new plants.