Hmmmmmmmm. About the watering. I water my jade when the soil looks dry. I'll water it gently, until water comes out the bottom of the pot. I have a shallow bonsai pot for my jade though, so it might be a lil faster than yours. But that's my general rule.
There's a thing that some people do where they wait for the leaves to stop feeling spongy, and look thin, but i don't like that one, because it requires touching the
plant. >.o i don't like to touch
plants unless i have to repot, prune, clean, or something like that lol.
If you want to propagate by stem cutting, make a slightly angled cut just below a node. Then put it in water. In a while, it'll probably sprout roots. You can use a rooting hormone too. I recommend taking the cutting, and just sticking it in soil. I'm not too sure how you'd get the stems to get any thicker than they already are though.
A way you can get more stems is to remove leaves. When you remove leaves, it leaves a scar. Most of the time, if you take good enough care of it, a new sprout of two leaves will pop out of the scar, and start a new branch.
Good luck with that!