DS,

Many plants will grow if given a chance to (i.e. not too hot and not too cool) - your Crassula ovata 'Gollum', Graptoveria and Kalanchoe will do so, so to call at least them dormant isn't correct. They're opportunistic growers, and your Aeoniums may do so, too. Sure, many plants shut down in the heat of the summer, but they'll grow if temps aren't too outlandish. With your humidity, maybe that would be a slower growth. Sans will grow 24/7, too, if you give them conditions for doing so (summer is one of their growth periods).

To your second to last paragraph, I'm finding that out, too. Many of my plants (the ones which aren't deciduous, at least) will grow in the winter, given the temps in the high sixties, some sunlight, and some water. Some plants, even if kept at constant temps, need a dormancy. Many don't.

Going back to your Sans, Crassula and Kalanchoe, at least, they'd grow as long as conditions are optimum for them to do so - if you can provide that year-around, they'll grow year-around, although during the extreme points of the cycle (winter/summer) they may slow down/stop for a while.

Not living in a cold, humid climate like Chicago, I cannot advise you specifically, but I can tell you the winter/summer thing is way over-rated. Many plants will behave opportunistically and grow happily year round if they have a good growing condition (not too hot or cold) and you don't overdo the watering thing. If asked whether most of my plants are winter or summer growers, I would answer both to 90% of them. There are exceptions that I 'accidentally' 'weed out' as I kill them off by treating them like everything else and gradually my collection becomes all winter-summer-makes-no-difference.

For example, Sansevierias, often grown indoors, seem to grow indoors happily year round oblivious of time of year. But even outdoors here in So Cal I have not noticed them growing more one time of year versus another, though flowering definitely seems to occur less in winter that summer... but does that mean they are growing better in winter than summer? Not necessarily. Many of my plants flower best when they have lost their leaves and are obviously in a 'slow down' period as far as actually growing bigger goes. Like aloes... my aloes grow way faster and are more active in summers (few exceptions) but most flower in winter. I notice aloes are considered winter growers... that is a useless description for me as they are obviously summer growers and winter growers, though grow slower in winter... they just happen to look great then.

Aeoniums definitely are winter plants, though and look unhappy in summer... they still grow in summer, though.

And some plants die if you water them in summer (I don't have many of those left, though), and some die in winter if you water them (I have none of those left as all my plants are outdoors and it rains like mad here all winter). But most plants deal with water year round for me and if I don't drown them with it, seem to appreciate it year round. Your Jade for example is a good plant for dumping water on year round.. it likes it no matter what the season and no matter what the temperature. To me, that is a 365 day grower.

And Dudleya spp. are known to look pretty bad in the summer if watered, too.

But yeah, I really identify with lzrddr here: "There are exceptions that I 'accidentally' 'weed out' as I kill them off by treating them like everything else and gradually my collection becomes all winter-summer-makes-no-difference."

When I first read about winter- and summer-dormancy at Highland Succulents (they make a big deal of it, and their site is listed in the resources "sticky" for people to learn about dormancy)... it scared me a lot more than it has turned out to matter for me. At least in my climate.

I noticed in my order from Highland Succulents that they use a soil mix fairly heavy in organics, though. So maybe it really does matter in their operation.