Paul,
Thanks for asking!
I have had no frost over the past 10 years. Because of this feature of my local weather, I potted up the newly rooted cuttings and kept them outside last year too.
The only thing I protect them from is the rain (like we had yesterday), I move all the cups under a cover. The temperature these days hovers between 55 (night) and 75 (day).
After the cups, they go into 1 or 2 gal pots. I wouldn't have enough room on my property if I transplanted that many cups into the 5 gal pots.
The fastest growers move into the 5 gals some time in the summer though.
In my case, I rooted 1 or 2 cuttings out of all new ones I acquired now, that would be about 50 or so cuttings. The rest I sealed and put in a fridge until the Spring (if the current cutting doesn't make it) or to trade later.
I do not root many duplicates since I am still trialing the varieties for the ones I would like to grow in the ground.
If I like it, I keep it, if not (it doesn't mean the fig is bad, it simply means my taste preference is different), I give it away.
As I mentioned, I really dislike starting the figs indoors. Rooting is OK but not to keep gazillions of cups and fighting with gnats over them.