Jades handle pruning very well, from light pinching to the extreme cutting back at the base. How you shape it is personal preference, but you can absolutely let the base growth fill in if you want. I personally like to give mine the look of a mature tree, keeping the trunk exposed, which makes watering easier, as well as inspection for bugs.

I do have to point out though that the soil your jades are growing in isn't preferable, as it doesn't provide adequate drainage and oxygen to the roots, which is vital to plants, especially succulents like jades. If you'd like to know more, search these forums and do a bit of reading on "gritty mix". Once you learn and understand the logic behind the use of a fast draining mix like the gritty mix, you take your plant growing experience to a whole new level. Rather than surviving, your jades will be thriving.

Joe

Anna, I agree that there may be too much organic matter in this soil. Research will show you a thousand options, but if that's not what you want certainly just switching to a cactus mix from a local nursery would help your plants to thrive and grow faster.

As to the styling, it looks as if previously the goal was to make them look like trees. If you want to continue that bonsai effort, trunk thickening is favored and growth from the base(with the intent of removing later) is good. On the second plant, I have the same sense as you- I would cut the trunk about half way up b/c it looks so arrow straight now. Then with the new growth, I would select two branches to fork and grow from there(three or four branches allowed to grow from one spot would cause and unsightly swelling). The repotting should come first, though.

Thanks Joe1980 and breathnez! I bought new medium for the plants. Ended up getting the Succulent/Cacti Potting mix from my local nursery. I'll re-pot them Saturday morning next week if I don't get to it today. Then maybe leave them along for a while before doing any pruning.

So the plan after repotting is:

1. Square pot - I'll remove the mini plant growing at the base of it. I do like the way he looks because he has a branch growing out quite low in the trunk. Maybe I'll just prune him a little to tidy up a bit.

2. Round pot - I might roll the dice and cut the trunk halfway. Then repot the top half when it's ready. The second half I'll wait and see how any new growth goes but breathnez has grew tips on selecting where I want the growth to go. Most likely to remove the new growth at the base too.

Also considering moving them indoors when the days/nights are colder…

I'm very excited about this. Happy that I can start by putting them in the right environment to grow more!

Oh and the smaller plants that have grown from the leaves, I'll re-pot them too and give them to my friends. Spread the love.

Soooo… I repotted one of the two Jades. Now, I'm a little worried if I'd done it right and if I got the right mix for it. Hoping to again tap into everyone's wisdom.

I'd removed the Jade from the pot there was a lot of roots. Mostly thin ones webbed on the outside against the pot. It took a while to get the old soil off and some of the thinner roots came off in the process. I know as much that losing the thinner roots when repotting is okay but I still had heaps left - definitely more than the 1/2 of what I started with. Oh and I didn't know I needed to rinse the roots either.

Then when I opened the bag of Succulent/Cactus mix from the nursery, it wasn't as loose or gritty as the mixes I've seen on the threads here. I didn't think I could leave the Jade out of the pot so I reluctantly repotted it with this mix.

And now I don't know if I should go to the shops, grab something to mix in with the new mix it's in and in the process further trim the roots.

Is that going to be too stressful for the plant to be repotted twice? It was cold and very windy last night so I've kept him in my kitchen in a well-lit corner for now so he doesn't topple over.

If I do prune the roots, is it right that it's around 2/3 of it?

I've put photos of the mix it's currently in, the plant in this new mix and also a Coarse Grit product I've seen and considering mixing to provide more aeration.

That grit looks OK (for what I can see in photo). I would try to get some perlite too, and mix them both with the cacti/succulent soil you have, about 1/3rd each (less soil than other ingredients). New mix doesn't look much different from previous - but difficult to tell from your photo.
Don't do any root pruning if you lost roots already, should be ok but don't trim anymore (unless they are dead or mushy/slimy). Gently take out of pot and put into new improved mix. It may be good idea to anchor plant, use some rocks at soil level and/or tie it if tall.
Here is current thread about anchoring (you should search this forum for more tips & some very good photos):

anchoring large plants

Keep it sheltered from strong winds, but good light is essential.

Rina