Hey there

I can't help you with the pruning, but I know a lot of people here hate cutting and pasting links, so I've linked four of your photos directly. I left out the {{gwi:691582}} blurry {{gwi:691583}}, if anyone wants to see those too. Good luck with your plant.

{{gwi:691585}}

{{gwi:691586}}

{{gwi:691587}}

{{gwi:691591}}

Thanks Citosa!

Also, does anyone know what the brown is on some of the leaves?

Thanks!
TJ

I would love to model my Jade plant off of the picture in the link.

Here is a link that might be useful: {{gwi:691584}}

TJ,

Your soil is highly unsuitable for the Crassula ovata, hence the leaves rotting. You need more porosity in your soil. In your reading here you'll run across some good soil recipes (the right one is the one that (1) works for you and (2) has the ingredients you can get)) - you should immediately remove your plant from that soil and let it dry for several days, or even a week or two - the plant will be fine. In the meantime, you'll be able to get the ingredients for the mix. It doesn't have to be special, but Crassula need drainage, and your soil doesn't have much.

My two pfennigs' worth.

Hey, TJ!

The first thing I'd do would be to replace that soil.

The brown marks on the leaves look like Sunburn - the bright stems indicate that this plant
has received a lot of light, which further leads me to this conclusion. I'd pull the leaves.
They don't indicate/cause any harm...they're merely unsightly. I pluck any leaf that displeases.

Pruning is rather straight-forward. Cut the long, skinny branches back to the main trunk.

At this point, I think it's more important to change the soil than to prune the foliage.
Jades can be pruned any time.

Josh