"I have a lot better luck sticking cuttings in existing pots vs. new pots with no existing roots to dry the soil regularly."
Wish I could take credit for this, but read it recently and it was like a light going on. I realized this is so true, looking back, and that I'd been doing it subconsciously in a lot of instances anyway. I think it's worth realizing as a complete, separate thought about propagating from cuttings, and repeating, highlighting. I sympathize with those who don't like the look of mixed pots though, I know my taste is off the wild edge of the scale. If it's "only for winter," maybe that helps a little.
Ooh Plumbago is pretty! Streptocarpella is easy to bring inside, Fuchsia, Impatiens. Bought a cute little Alternanthera (Calico plant) a few years ago that makes a tiny little bush a few inches tall in the annuals section but it's much better as a potted plant (so you can actually see it) and is fine coming inside for winter.