In the field, many plants develop an underground stalk that doesn't rot out. In pot culture, an underground stalk can be a site for rot when a plant is overwatered. Repotting can also traumatize fine roots and I tend to mist the repotted plants daily to aid water transport until the roots regrow. I still like small pots but only when a heavier soil is used. I like to use a pot that fits the root structure.
Many succulents respond well to frequent light waterings.
Many succulents fare well when small amounts of moisture remain inside the pot while the surface of the soil is dries after a day or two. The plant may have lost its root structure or is dormant. In this situation, misting should be used to keep water contact light. As plants respond favorably to good watering practices, the roots will thrive giving the plant vigor and size. The stems thicken and roots age.