Don't take this wrong, because I want to help and not offend; but a 60 year old jade when not severely limited by cultural conditions, even when grown in a pot, would have a trunk at least as thick as a basketball. Last weekend, I worked on 2 jades that were recently gifted to Gloria S, the president of the Saginaw (MI) County MG's club. They were both 7 years old and had much more mass than the plant in the image, and prior to her receiving the plants, they hadn't been particularly well-cared for.

My guess is, your plant has suffered severely from root congestion, periodic intervals where a large fraction of the root mass was affected by rot, insufficient light, and probably nutritional issues that include but aren't limited to a high level of dissolved solids (mineral salts) in the soil and a badly skewed nutrient ratio; that is to say some nutrients are likely so over-represented in the soil solution they block uptake of other nutrients. The good news is, that's all fixable if you're amenable to entertaining a plan that if followed will turn your plant around (and very probably shock you with its response).

The main questions in my mind are, how do you feel about my blunt assessment? and are you down with putting a 'turn around plan' in play?

Al

I want to do what is best for this plant. When I repotted I was surprised by how small the root ball was. I really expected it to be larger.

That's because the soil regularly stays wet for periods so lengthy it rots the roots back to nearly nothing. Then, all the plants energy goes into replacing those rotted roots, something the plant must do before top mass can increase. That cyclic death & regeneration of roots essentially accounts for the plant's entire allocation of energy, which is why the top hasn't grown.

You can treat this two different ways. One is to nurse the plant through until next summer (probably June, but it depends on where you live) and do a full repot into a soil that allows you to water correctly. Jades are one of the easiest plants to repot, and they respond well to root pruning. In fact, you can start cuttings of jades that are as large as a softball, so you can cut the top back very hard to an attractive framework and cut the roots back to a point where you can remove ALL the old soil before you repot into something that allows you to water correctly. Jades LOVE this soil

so if you're amenable to putting something like it together between now & then, you'll be glad you did. You can use it for all your succulents, cacti, houseplants, and other long term plantings you might have.

Not a jade, but close. Note the soil:

The second thing you can do is treat this as an emergency repot. If you think the plant won't make it until spring, you CAN repot now, but it is a little more risky because of the plants low vitality level, which means energy reserves are low. Still, none right it shouldn't be an issue.

Al

The plant will make it til Spring, but I now see I picked the wrong time to repot as I did that a month ago.

But I'm wondering as the repot was so recent, should I try again so soon?

What is in your soil mixture?

There's a big difference between a repot and potting up. Read more here.

Too, understanding the impact soil choice has on your ability to keep your plants happy probably deserves being labeled the most important part of being a proficient grower. At least 90% of the issues people come here seeking remediation for are soil/root health related. You can't hope for a healthy plant unless you can maintain a healthy root system. This will explain why soil choice is important and provide recipes and some direction.

Al