I realize I'm late to the conversation, but my viewpoint is a little different from the rest when it comes to watering jade plants. I never squeeze leaves or stems, I check the soil. It should go dry or almost dry between watering, but not stay dry for any extended period. Based on experience, I have a pretty good sense of when that happens. It helps a lot when the plants are getting good light (indoors that means daily sun) because the sunlight promotes the drying out of the soil.
With jade plants and other succulents the watering mostly has to do with respecting the plants' natural preference for alternating wet and dry conditions. They do not thrive when the soil stays one way or the other. This is a bit of an oversimplification but it serves as an excellent guiding principle when you're in doubt about when to water your succulent.
Note that the top layer of soil will always appear nearly dry but a few inches down the situation is more informative. You can use a moisture meter or your finger or a chopstick to get a good idea. I like to time my repotting a few days after watering, about when I expect the soil to be going dry, and that's a great way to confirm the situation visually.
