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I live in northeastern USA - it snows in the winter and tends to hit around 35C in the summer. It's always humid.
I have a Ficus benjamina that was started as an air layer from a larger tree about 5 months ago. It has spent the summer months outside but in roughly 6 weeks I should start thinking about bringing it back inside for the fall/winter. I would like to do a drastic top chop now that tree is established in it's own pot and healthy. The question is when should I make the cuts, knowing that it's environment will be changing significantly in the near future? Do I do it now and assume that ~6wks is enough recovery time? Do I wait until I bring it inside and it's acclimated? Should I wait until it's inside simply because there is a lower chance of infestation?
Thanks.

I think it does not really matter, but probably would do it now. I have just chopped about 75cm all around from our ficus in preparation for winte,r to allow it to reciver before it goes back into the dark dry place for winter.