All throughout the Old testament , the Hebrew Scriptures do we find examples of Satan interfering with Gods plan
Apart from the story of Job, can you name one event in which Satan is explicitly mentioned as the evil doer in the OT? I don't think there are any that can be ascribed to Satan without reinterpretation given in the NT or in Watchtower literature (but I may be wrong). Apart from the book of Job, Satan doesn't seem to play ball in the OT. And why would he? Yahweh managed all the killing, maiming and raping just fine by himself.
As for 1914 and Satan suddenly waking up: I guess he fell asleep before. After all Jdib had his long ass 7th creation day Sabbath, Jesus was sitting on his hands doing nothing until 1914, so why would Satan be all busy then?
But yeah it doesn't make any sense at all.