First, stop panicking.
Don't rely on a moisture meter to tell you when to water as they measure electrical resistence in the soil. If the soil has a high salt content, the moisture meter will say to water. Oops! Its much better to use the plant as a guide.
Turgor is the pressure of water within a cell pushing out against the cell wall. When the turgor pressure is low, plants wilt... and they need a drink. Jades don't wilt, at least they shouldn't, but the leaves will feel softer than usual. As you just watered, feel the leaves. They are hard and slick - no water needed. But, when they start to soften, it is time to water.
As you just potted your new Jade into a bigger pot, it will take longer to need water. Don't even thing about checking that calendar!
Transplanting to a new home (even with the same light) and transplanting to a new pot (hopefully, you used cactus soil with added perlite) are major events in this plant's life. You will have to forgive it for being a little grumpy for awhile. Overall, it looks good. Physical damage is par for the course for an outside plant.
BTW, there is no way your plant is 35 years old. If it were, the trunks would be at least 3 - 4 inches in diameter, even in a small pot. Maybe 3 - 5 years old.