@mmgsport Welcome to All Things Plants!
I used to grow a couple of small Jade plants but lost them all to rot during a rather rainy summer a few years ago; they were not happy with the high humidity and so much rain. The stems of your plant pictured sure look like mine when they got soft and turned black from too much moisture. I never pruned my jade plants so I can't offer advice about that but I did have one that grew a decent sized trunk which I attributed to being in a very small container. When I finally got around to re-potting it, it's roots were totally filling the small container. When visiting southern California I saw some really large and beautiful Jades grown as landscape plants and shrubs and it sure gave me zone envy.
We have photo's and information in the ATP plant database regarding the Jade plant. If you scroll all the way to the bottom of this page you will find comments from a few members who've had experience growing them.:
Jade Plant (Crassula ovata)