I have cuttings that have rooted and grown quite a bit using the bag method. And now they are rooted enough to pot up. But since it is late summer here, I am not sure whether this is a good idea? Or maybe it is safe to pot them into a container that is relatively the same size as the bag they are in now?

Don't imagine they can put on many roots to fill out a new pot by dormancy time. Nights are already dipping into the 50s. I don't want the cuttings to be sitting in excess and or soggy pots during the winter. Although I can mix a very very quick draining medium.

Unless of course, I try to overwinter them inside? Probably wasn't the best idea to root them when I did, but what can I say? My timing for remembering wanting to grow figs again was late and I couldn't bare waiting any longer ha!

Throwing 'em in the ground is not an option due to my zone.

I would probably pot to a size similar to what it came out of.  Just slightly larger, as you mentioned.  It will be easy to shuffle in and out of the house during the cooler nights as late fall approaches.  Hopefully, it will harden enough by late fall and it will go dormant without any issues.  I think that is the easier approach, rather than keeping it awake all winter.

That is the direction I am leaning, FiggyFrank. Although, I wasn't planing on bringing them in at night, only moving them finally to the garage once temps dip too low and they go dormant. But maybe I should bring them in at night for a bit just to give them a little time to acclimate to their new pots? It'll get warm again before finally cooling off here. It's been such an off summer. I am just fortunate to have some tomatoes!