It all depends on what you have to work with.
I put plants out starting in November, and put at least one plant outside every month up until this day. Mostly clones, but a few seedlings as well. I can tell you that the younger and the more unhealthy the plant, the more difficult its going to be for it to adjust to a cold winter. For older more established plants, its easier for the rootmass to retain heat and moisture, as well as use stored energy to heal/reveg itself. freshly sprouted seedlings won't make it and if they do, your results will be piss poor, same for freshly rooted clones. Every plant that I put out up until the beginning of June wanted to flower or did flower. I didn't move plants around to keep them out of the harsh winter, or fret over feeding or watering them. I pretty much left them at the mercy of a long natural winter. The buds were a bit sparse due to the cold, growth was stunted at times like when they were snowed on, or was just slow in general when it was freezing outside. Dry frosts after hard rains hit them the hardest. Plants that got more daily sunlight produced way better and way more than others. Not a single plant that I put outside died,
, I even tried pulling up a few and throwing them away, but their roots grew into the hillside and they persisted. All the plants I put out were in pots. They were more exposed to extremes like wind chill, especially the root mass. I am certain that plants established well in the ground would fair very well in a winter cycle. I didn't add any supplemental lighting, the whole fiasco was an experiment to see what would happen, and determine the best steps I could take to improving conditions to make it ideal for them to flower all winter through. Its fairly easy to pull a cover crop in the summer, even a few cover crops if you have the materials and space.
So from all of my experimenting over the years, with outdoor perpetual harvests, I feel I now know what I need to do to harvest prime winter spring summer and fall crops.... as often as if I was flowering them indoors. For me, supplemental lighting would be necessary, as well as having them in the ground and fairly well insulated at topsoil level. Air circulation, humidity, and ambient temperatures are important as well. What exactly your plants would need to do the same would be completely dependent upon what strain they are, what your climate is like, what you have to work with, and what you actually DO,