Interesting question(s), while I don’t know for sure I believe Satan’s sin was so well it was done in much greater knowledge (and turning from God) than our natural death as sinners...however I cannot really answer fully!
Second question. I would say that they may have known the truth, and been drawn by the Holy Spirit, but weren’t really saved. A very dangerous place indeed, as they will never be saved!!
Heb 6:4-6 doesn't merely say "drawn by the Holy Spirit" but rather "shared in the Holy Spirit."
It also doesn't simply say to know about the truth, but is much more experiential: "tasted the heavenly gift" and " who have tasted the goodness of the word of God and the powers of the coming age".
(This hardly describes just God-fearers, Christian wannabes, unsaved church members & unbelievers)