It’s better to release them as close to the debates as possible.
Agree. Kind of like “Don’t fire until you see the whites of their eyes”.
Assange is smart enough to know that, given sufficient time, the media would shield Hillary from one big dump of data. What he’s doing is dripping the information out in batches. This keeps the story fresh and softens the target for the main thrust which is yet to come.
Correct. Best timing is in batches 2-3 days before each of the debates for maximum exposure, and then two weeks before November 8th for a final "October surprise".