Hello Jademan, I have rooted many Jade stems. What works for me is to use shallow and wide containers with drain holes. Media mix is gritty. I usually do cuttings in mid Spring, that way I know outdoor light is getting longer. I never root them in water. I do follow your steps, callus the cutting then stick it in the media. Container is in part sun/shade but it is outdoors. So it will also feel the temp fluctuations and eventually harden the plant to its outdoor location. I try not to do cuttings in late Fall to winter. Though jades are good mild winter growers, when it comes to rooting, it needs sustained warmth at the rootzone to encourage rooting and good light for the rest of the plant. While it is new and young, it may be thistier once roots has started to grow well, so having a gritty, well draining media is important, especially come summer time when heat is intense and light levels much stronger. It will be by then drinking more to sustain its growing needs till it gets more fully acclimated.
Our growing areas have its own microclimates, ours is very dry, no summer rains, dismal humidity so I can afford to step up watering here at that time. It maybe different on your side but nevertheless, make sure you have well draining media and good light for your young cuttings till they slowly mature and harden to your growing area.
Here are some of them, all grown outdoors.