I would suggest that the way you phrased your question from the beginning presents some sort of animosity to the Bible? One cannot question whether one should be proud about their holy book unless one is suggesting that there is a reason not to be proud of the book. I believe by asking whether or not someone is proud of the book questions the book and its message from the beginning. And whether or not this is where you are coming from I believe that the question is poorly phrased.
Leaving whether or not you are critiquing the Bible in some negative fashion, I am going to discuss some of the questions you have raised about the book in general. I believe from what I have read that you consider the book to be petty, repetitive and boring. I am sure that you think many other things about the Bible but I am going to tackle those three primarily.
As regards to the question of pettiness, I think I can account of the pettiness of the Scriptures in two points. I think one of those points is about the people who are in the Bible. First I would like to state that the people who are in the Bible are complete characters. They often show both the good and the bad of these people so we get well rounded and not flat characters, more indicative of human life and not some manmade myth. David, who was both and adulterer, murderer and king was considered a man who knew how to please God. So as opposed to the Enlightened Buddha, or the amazing prophet Joseph Smith, or many other various people in religious texts, we get heroes with warts and all. Secondly, I think we are confusing who the actual hero of the Bible is. I believe that the hero of the Bible is God himself. This Bible shows a God who does not change. He has certain standards that he expects yet he is merciful, forgiving and loving as well. It is the petty humans who keep confounding God and seeking other pleasures, or actively trying to thwart God who create the problems. The Bible shows a cycle of these human beings throughout time . But God himself is consistent. The God of the Old Testament still forgives people, ask Jonah. And the God of the New Testament still has punishment, read Revelation.
As regards to the repetitive question, I think I can cover that through some of what I have already alluded to, and through some other scriptures. First let's take a look at the Gospels. Ultimately much of the story is repeated over and over again through four books. Three of them often have the exact same stories. But one needs to dig a little deeper to see that there is something else going on there. Take Matthew and Luke. Both have stories often identical. And for the sake of discussion, both texts in this case have genealogies of Jesus. Why have two books doing pretty much the same thing? But if one takes a look a little closer, one can see some significant differences. If you have read through the Bible and have read Samuel, Kings and Chronicles as you have alluded to, you would notice that you should recognize many of the names in the Matthew genealogy? Why would this be? Because they are the Kings of the books in the Old Testament stories. Matthew is very much interested in presenting Jesus as King, even referring to the sign on the cross that states about Jesus being King of the Jews. Luke, on the other hand has a genealogy that goes backwards all the way to Adam. Why do this? Because Luke wants us to be aware that Jesus was fully human, not some spiritual force but of human kind, as Adam was the first man. And if you read through much of what is written in Luke, Jesus refers to himself as the Son of Man a lot. John on the other hand was interested in us knowing that while Jesus was human, Jesus was also God. There is the part where Jesus says before Abraham was, I am. That was in direct reference to the God of Moses who told Moses to refer to himself as I am that I am. The Jews obviously knew it because their reaction was to attempt to stone Him for being a heretic. But John wants us to see that is who Jesus was and who He claimed to be. Matthew focuses on Jesus being a servant. Each of the Gospels repeating a lot of the same things, but doing so in order to present different sides to who Jesus was.
Aside from the Gospels one can refer to the repetitiveness of the Chronicles, when compares to Kings and Samuel. But even when the stories are similar, there is often a different focus. It's not simply repetitiveness for repetitiveness sake. Finally I think the Bible can be repetitive when it wants to show how inept humanity often is. God's chosen people required the law given to them not once, but twice. Deuteronomy literally means a second giving of the law. One was given while they were roaming the wilderness, and one before they were finally going to enter the promised land. And once they do enter the promised land, how soon they forget again the law and go about worshiping other Gods. It takes a generation and they are already doing bad things. And Judges is a cycle of this happening again and again, which shows our inability to follow the law, and shows God's consistency, not only in judging, but in keeping his promises as every time the Jewish people turn to Him He brings them back to Himself and restores them.
Finally I am going to tackle the boring aspects of Scripture. Yes Scripture can be boring at times. I don't think one can go through the Chronicles without drifting off once or twice. But I think that two things can be seen. One I refer you to the genealogies that both Matthew and Luke wrote and how those two genealogies were reflective of larger themes that the authors were trying to show. So you can't just look at the boring parts and assume that they were just thrown in there without any good reason. Furthermore, I think this reflects poorly on your reflection that a plain reading of the text should be able to give you everything you need in a text. That somehow a text should be subjected to some plain meaning text. And while I am sympathetic and even believe that much can be gleaned from a plain reading of the text, as you alluded to Ecclesiastes, I believe that the poetry and philosophy in their are deep and profound and translate very well into the English language; I believe there is so much more to be gleaned by going deeper into the text. Commentaries are very good for such a thing.
I cannot believe for a second that the very first time you picked up a Shakespeare text you said to yourself, I am not going to read the side notes, or the commentaries or the introduction, or even a cliffs notes version of the text and then had an instant understanding of Shakespeare. You probably had to read at least one if not many of those your first time through. And then maybe over time it got easier and easier because you gained a feel of who Shakespeare was through all of his writing. But the Bible makes that even more difficult, because you have these ancient languages from almost 4000 years ago putting into writings these ancient stories from 30 to 40 authors. To say that you should just pick it up and have a plain meaning and understanding in one try is hubris at its finest.
I remember taking a class in Ovid's Metamorphoses. At one point we were given different translations of the Metamorphoses and then were instructed to compare and contrast. One would think that one central focus would be there, but often times one could see very different things emerging from the different translations. We cannot hope to understand all of these parts, including the boring ones, without some sort of contextual help, historical context, or understanding.
So yes the Bible shows pettiness, as it shows real people doing real things; and yes the Bible can be repetitive as it often shows different perspectives, or it reflects well on the God who never changes and who loves and seeks reconciliation with Himself and humanity from beginning to end; and yes the Bible can be boring, but that doesn't mean that there isn't some significance to what is written, you may just have to dig a little deeper. And one cannot hope to understand everything through a plain reading of the text, even historical, philosophical or linguistical resources must be used to add breadth and depth to the beauty of Scripture as with any great, epic or historical text.
Ultimately when it comes down to it asking whether I am proud of the Bible as my holy book is asking the wrong question altogether. If I believe the Bible is God's love letter to us, trying to reconcile broken humanity to himself, I have the ability to reject or accept that premise from the start. But as I believe that the Bible is that love letter; I am astounded at the God who loved us so much that he would send His Son to a horrible death, the death on a cross, to reconcile a broken people to himself. That amazes me everyday.