Thanks for your interest. To answer your questions,
1) Care: the zone I live in does get below 40 deg., but this winter never went below freezing. For the winter, I moved my succulents onto a covered landing where they'd be protected from rain and wind, but still got at least a little sun. If the night was going to be below 40 deg. I covered the succulents with a light sheet, although I admit I didn't do this regularly.
2) I water, fairly lightly, about every 2 weeks. I've read that succulents and cacti need very little water in the winter.
3) I last watered about a week ago, again not very heavily. They are planted in a good soil meant for cacti and succulents (they were only planted last summer, and I'm new to succulents except Jade plants). And yes, there is a good drainage hole in the bottom of the pot.
4) I have them outside (I have such a tiny apt., with not much light, that I didn't have room to bring them in).
I've included (probably too many) photos of the whole succulent bowl. Taking a closer look at it, none of them look great. My guess is too much cold, and not enough sun or water. I think it's warm enough now that I can put them out in full sun and give them more water, but I don't know if it's too late. I also have a regular jade (whose leaves are starting to look puckered), two miniature jades, a ripple jade, and one other whose name I can't find: straight leaves are 3-4" long and are curved in on themselves. Other than the Crassula ovata, they are doing well. I've also included another picture of a succulent (whose name washed off my makeshift plant identifiers). I think it also looks pretty good.
Lastly, can you identify the taller plant, and is it getting too leggy?