As Ken said, using an existing hole to get to your attic will allow you to get anywhere in the house.
Since you are doing outlets on 2 finished floors, I would suggest sticking to the wall mount boxes and trying to leverage cold air returns or closets to get the cable into rooms, then run behind the floor boards until you want to pop out for a box.
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"Wake up, Luigi! The only time plumbers sleep on the job is when we're working by the hour."
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