Should I remove the medium before I leave, or will they be warm enough for now and if it doesn't fill, I can just remove it later?
I'd leave it. As you noted, it's been a warm October, and my bees are still very active and working the goldenrod and asters.
My other hive .... Will this be enough to survive? I will feed in winter, either dry sugar or hard candy.
Hard to predict. Last winter I had two strong colonies die, one with plenty of stores remaining, while a dinky hive from a late-summer swarm survived.