I think its a good idea to question the Bible, I think the spirit in which you question it would be more of a concern. Most of us have questions, principally because the language scripture is written in, is different from most who are reading it, unless your native language is Aramaic, Hebrew or Koine Greek. So in that regard, translation, context, culture at the time (hermeneutics) create a disconnect in understanding these writings.
For this reason there are institutions of higher learning that help understand the history and the discipline of interpretation (exegesis).
Having said all that, the bible is not an intellectual exercise, its a spiritual one. What this means is that scripture is coded to those who have a password to unlock it. This password is the Holy Spirit.
1 Corinthians 2:12-14
12 Now we have received, not the spirit of the world, but the spirit which is of God; that we might know the things that are freely given to us of God.
13 Which things also we speak, not in the words which man's wisdom teacheth, but which the Holy Ghost teacheth; comparing spiritual things with spiritual.
14 But the natural man receiveth not the things of the Spirit of God: for they are foolishness unto him: neither can he know them, because they are spiritually discerned.
Consider this, Satan is an Angel, who was created in the presence of God Himself, Angels don’t suffer from memory problems like men, but they are spiritual beings. The point is, demons are not inspired by God anymore and therefore they lack spiritual insight to what God has said. Even though they understand words and can tell you what is written and where it is, they don't know what scripture means.
From the time they were cast out of Heaven they lost access to the password or understanding of Gods words.
Revelation 12:7-10
7 And there was war in heaven: Michael and his angels fought against the dragon; and the dragon fought and his angels,
8 And prevailed not; neither was their place found any more in heaven.
9 And the great dragon was cast out, that old serpent, called the Devil, and Satan, which deceiveth the whole world: he was cast out into the earth, and his angels were cast out with him.
10 And I heard a loud voice saying in heaven, Now is come salvation, and strength, and the kingdom of our God, and the power of his Christ: for the accuser of our brethren is cast down, which accused them before our God day and night.
The first prophesy of the coming of the Messiah took place in the Garden of Eden at the time of Adam and Eve's ejection.
Revelation 12, establishes that Satan was cast out of Heaven and his names in context. Its established that Satan was in the Garden, he was present when God said the Messiah was to come.
Ezekiel 28:13-14
13 Thou hast been in Eden the garden of God; every precious stone was thy covering, the sardius, topaz, and the diamond, the beryl, the onyx, and the jasper, the sapphire, the emerald, and the carbuncle, and gold: the workmanship of thy tabrets and of thy pipes was prepared in thee in the day that thou wast created.
14 Thou art the anointed cherub that covereth; and I have set thee so: thou wast upon the holy mountain of God; thou hast walked up and down in the midst of the stones of fire.
Genesis 3:14-19
14 And the Lord God said unto the serpent, Because thou hast done this, thou art cursed above all cattle, and above every beast of the field; upon thy belly shalt thou go, and dust shalt thou eat all the days of thy life:
15 And I will put enmity between thee and the woman, and between thy seed and her seed; it shall bruise thy head, and thou shalt bruise his heel.
16 Unto the woman he said, I will greatly multiply thy sorrow and thy conception; in sorrow thou shalt bring forth children; and thy desire shall be to thy husband, and he shall rule over thee.
17 And unto Adam he said, Because thou hast hearkened unto the voice of thy wife, and hast eaten of the tree, of which I commanded thee, saying, Thou shalt not eat of it: cursed is the ground for thy sake; in sorrow shalt thou eat of it all the days of thy life;
18 Thorns also and thistles shall it bring forth to thee; and thou shalt eat the herb of the field;
19 In the sweat of thy face shalt thou eat bread, till thou return unto the ground; for out of it wast thou taken: for dust thou art, and unto dust shalt thou return.
The setting of this prophecy in Genesis 3, provides the necessary background information we need to understand the full implications of God's pronouncements in these verses. Adam and Eve were still living in the Garden of Eden. Satan, speaking through a serpent, had just deceived Eve into eating the fruit of the tree of the knowledge of good and evil. She, in turn, had persuaded Adam to do the same. These sins demanded the judgment of God, which He expresses as curses that would result from their disobedience.
What we see is that God did not curse them—they cursed themselves! Because of sin's predictable course, God merely voices the consequences of their actions in prophetic terms. This prophecy, then, includes Satan's ultimate guilt and punishment, mankind's battle of the sexes and struggle to survive, and the need for a Savior to repair the damage they had caused. What we see in microcosm is the plan of God!
Satan did not understand what the Messiah would cost him. He did not know whether or not to crucify Jesus even though it had been prophesied for thousands of years in advance.
Mark 8:33
33 But when he had turned about and looked on his disciples, he rebuked Peter, saying, Get thee behind me, Satan: for thou savourest not the things that be of God, but the things that be of men.
1 Corinthians 2:8
8 Which none of the princes of this world knew: for had they known it, they would not have crucified the Lord of glory.
The point is, Satan did not know if he should not kill Jesus, not because he can’t read, or that he did not hear God in the Garden or even Jesus who discussed the reason for his coming, the work and even his death. The point is that he no longer has the password.
it nothing wrong with questioning the scripture, you should. But it should be about seeking understanding and learning the truth, rather then doubting the veracity of scripture.