Do I trim and plant it deeper? Roots growing on the sides.

You can leave them as is, plant them deeper or cut off the side stems and make more. If you leave them, the current stems will continue to grow and keep sprouting more roots. Eventually there will be additional stems to fill in. If you plant them deeper they will look a little less weird and root all along the buried stem.

They've already been topped. Now they're responding to losing their heads by growing multiple new tops.

I just don't know why roots keep on growing on the sides.

Roots will be caused by escessive moisture, and over watering.

Aeonium2003 said:Roots will be caused by escessive moisture, and over watering.

If you don't like the roots, you can simply just pull them off, and they should come off easily.

GummyBear said:I just don't know why roots keep on growing on the sides.

It usually means the succulent isn't getting enough water from the soil so, if its humid enough aerial roots can absorb some moisture from the air.

Edited to add: not necessarily an underwatering problem but I root problem of some sort.

I just leave them alone. In time once it gets much warmer, it will just naturally dry out if your area is as dry as ours.

I do like seeing them in my plants like my Aeonium, it shows me it is waking up from its dry season slumber when Fall arrives.

Your plant is still very young..I would be more concerned with its lighting needs. Hope you can position them closer to a south facing window.

This is what they look like 2 months later. Don't seem to be growing much. The used to be indoors where the temperature is always between 68 and 71. In that greenhouse it sometimes drop to as low as low 50s at night. Daytime temperature is usually in the 60s. Wondering if the temperature is slowing down their growth or they just need a bigger pot.

Those temperatures are well within the comfort zone of your succulents, more or less what we experience at this time of year, and they seem to be going stronger than ever.

It's not always just the temperature ranges. Shorter days also slow down growth. Because light is the source for producing chlorophyll, some plants will sort of try to sleep instead of grow until the days are longer.

It looks okay to me, as it gives colorful cold stress colors..I love that stage.

No need for a bigger container, still enough space there. It can handle temps in the 30F range as long as it gets good sunny exposure and kept drier at this time of the year.

Your plants do look strong & healthy.
As others mentioned above they grow very slowly in winter.
When the days get longer and warmer then you need to decide.
If you bury them deeper it will be in a tall pot, with too much dirt,
and they will always be lopsided.
'If they were mine': I would wait for warmer weather. Then I would cut off the healthy rosettes. Let them heal (callus) for a couple of days and then set them on top of new pots with holes. In new, well draining soil mix. In a few weeks they will be making new roots and in a couple of months you will be able to see the new growth.
The smaller rosettes will need smaller pots.

Yes they look pretty good to me?

These are the temperature range. I always worry that plants to the rear and bottom does not get enough light.

When those temps drop near freezing (like Feb 24) or are forecasted to do so, it's probably a good idea to hold off with the water.