Over the years I have somehow amassed a fair-sized collection of small pots...from about the size of a bathroom sink toothbrush cup to maybe a quart or so. Most of the plants I have would outgrow them quickly. I do have some succulents that weren't killed by being in the dungeon (basement) over the winter that I have earmarked for some of them. But I wonder if there are other lilliputian plants that might be appropriate for these small containers that could also put up with being on the dry side after hours in the hot sun. And since I'm asking for everything, winter tolerance in a pot would be great but I could move them into the poorly lit basement. Anyone have suggestions/recommendations?

Oh, and extra points if it flowers, provides food for bees, or some other function. :D

I'm not sure there are many succulents which would tolerate spending the winter in a dark basement, but some people have adapted to make this work for a variety of plants (I am thinking specifically of @simcactus). The key is to withhold water, water less often, and/or water short of saturation to convince the plants to go to sleep for a while. I have zero experience with overwintering and would be the last person you'd want to ask about it, beyond those vague generalities.

If you have space by a sunny window, you can overwinter all kinds of small succulents inside. Some of the small succulents I have kept behind just such a window are Haworthias, which range from dwarf to small, with individual rosettes reaching about 4 inches on the more common plants. Here's a pictorial sampling of the Haworthias I have going in small(ish) pots, some of them recently separated offsets, some established for a bit longer... all perfect plants for a sunny windowsill. They should all flower at least once a year.

4 inch pots


5 inch pots


The bigger Haworthias can be kept in smallish containers if you're willing to depup them every so often. Here are some clumps allowed to proceed further than most people usually go. These could all go in 6 inch pots indefinitely if you periodically removed some of the competition. Haworthias appreciate a little protection from the sun (so maybe less than half a day if they are going to be outside) but they tolerate the sun here given very mild summer temperatures.

8 inch pots



Small cacti are excellent for small pots under the conditions you have described, but these are also very demanding about light (unless you can lull them into a winter trance state). Most are ideal for a sunny windowsill. Fast drainage and discipline with the water is essential for these and most other succulents.

There's a bunch of bumpy aloe hybrids that will do fine forever in a 6 inch pot if you periodically depup them:



These plants require strong light for good color but maybe some of them would do okay for a while in a dimmer situation. They are very well behaved here and there's a huge variety of colors and textures.

Al

I have over 300 plants that go in my basement every winter. I lose s few each year, but am getting better. I water every three or four weeks in winter. Some more, some less. I have two window that they all fight over. Most Haworthias go on the bottom shelf. They get leggy ( out of shape) but survive.

These dunce caps (Orostachys iwarenge) winter well outside and are in full sun. Bees love the flowers that bloom in the fall.

You might try some herbs
I have some thyme that stays small and will winter-over well
there are also some perennials , I have mini coral bells , erodium and stachys, but they like regular watering.

also hen &chicks