* As the bees draw out the comb in the 2nd brood chamber, should I plan on adding honey supers?
If they're 80% drawn sure. If they draw that first super out and fill and cap it, put a second one on you might be able to harvest off the first one if the second one is 1/2 full you could leave that for them. However, don't count on harvesting anything.
* If I do, is this the honey the bees use for the upcoming winter?
Could be, that's why you probably shouldn't take any honey from a first year package hive unless they're really strong and have multiple drawn and some capped supers
* If so, how would they move up into the super over the winter? I thought they would/should stay in the brood boxes.
They'll move up if they are running out of stores. It's a great insurance policy for you and them. I've never gotten honey from a first year package without supplementing them with drawn frames, bees and brood.
* How would I know if they have put up enough honey that I could take some (if at all)?
Talk to some local beeks who better know what kind of flow happens for you up there late in the season.
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