Thoughts on Bible Reading Habits and Messianic Prophecy

Unbelievably, I have never read the Bible. The whole Bible, that is. Oh sure, I've read all the actually entertaining parts numerous times. The first half of the Old Testament is pretty good. Lots of great stories, sex, violence, miraculous acts... even if I weren't a Christian, it would still make a good read. And I actually have read Deuteronomy and Numbers, believe it or not. It helps to be able to get momentum with the excitement of Genesis and Exodus and to know that you have lots of juicy bits coming up in Joshua and Judges afterward. A similar thing could be said of the Gospels and Acts, lots of great stories, plus you get to read about Jesus, who is awesome, humbling, and funny (no, you read that right). Yeah, much of the rest of the New Testament can get dry, but I have read it nonetheless, either force-fed through years of religious experience or due to my own theological curiosity. The parts of the Bible that I usually skip are the middle bits. Growing up, I would skip all the middle bits. The books of wisdom as well as the books of the prophets. As an adult, I have found the books of wisdom (Psalms, Proverbs, Job and Ecclesiastes) to be some of my favorites. It is a literature scholar's dream really, and I am surprised that it took me so long to recognize how beautiful much of it is.
Recently, I have decided not to stop at Ecclesiastes and actually move through Song of Solomon and into Isaiah. Surprisingly, I have found it pretty interesting, though it would be hard for me to put my finger exactly on what the appeal is. I think part of what I am enjoying is that it is a book that seems like a puzzle where I have been staring at some of the pieces of years. Certain passages are as familiar as any, mostly because they have been referenced a million times in church songs ("...soar on wings like eagles.." etc) or because they have been referenced in the New Testament, in sermons, and in Christmas songs due to their messianic nature. It is this latter type of verses that I have been curious about of late. I have to admit, I can't help but hear Handel when I read "and the government will be upon his shoulders" and so I can recognize many of the verses in Isaiah that Christian theology takes to refer to Jesus Christ. The problem is that many of those verses seem... well, arbitrarily picked to foretell the coming of the messiah. In fact, if you cross reference them with other parts of the Old Testament narrative, many of them seem to speak of certain events and characters from Jewish history (namely Jewish leaders and prophets); that is how many Jewish commentators interpret the passages as well. Are they messianic in that they foretell the coming of someone who will ease Israel's troubles? Sure, but that is not necessarily such a cosmic thing as we might make it out to be. Sometimes I can't help but feel that the Christian writers have tried to shoehorn Jesus into certain Biblical passages and make give them greater prophetic importance than they originally had in ancient Israel. I would be interested a debate between Christian and Jewish theologians on the nature of messianic prophecy. I suppose it would ultimately fall apart at a certain point though, because in order to truly function, you would have to have the similar perspective on the nature of Christ (at the very least from a historical perspective). Either way, Christ himself seemed pretty firm on trying to dispel Judaic misconceptions of  what "a messiah" was supposed to be.