Hello David! This is a really great question, thank you.
Let me start by think about the first ideas you mention, about how do we know Jesus and what does that mean. Firstly, I believe you are totally right in the difference you mention: It isn’t the same knowing about someone that knowing someone, and the Bible does speak about the latter being an essential part of our relationship with God, although knowing about him also has its place.
The Bible points us to Jesus. Jesus himself makes the point that it isn’t enough with just readings words written or printed in a book: “You search the Scriptures because you think that in them you have eternal life; and it is they that bear witness about me, yet you refuse to come to me that you may have life.” (John 5:39-40). Life is found in Him, and the Bible has the essential task of leading us to know Jesus. But it isn’t the Bible alone. Hebrews 4 speaks of the Word of God as living and active, able to go deep in our being. Perhaps related to this idea, in Ephesians 6 Paul tells us that the Word of God is the sword of the Spirit. The Bible is not just a collection of words, but God can use it through his Holy Spirit in order to change us and most importantly in order to lead us to real knowledge of Jesus, in order to trust Him. In John 10 (and I promise I will stop throwing verses at you now! ), Jesus says “my sheep hear my voice”. I believe that is true, and that the more familiar you get with Jesus and the more familiar you get with the Bible, the less reading it is going to feel like a one-sided conversation.
If you continue reading it, and meditating in it (Taking time to think what does it mean and what does it mean for your life), I am sure you will naturally find yourself praying through the Bible, introducing verses in your prayers, etc. It may be that you are praying and God may put a specific passage in your heart, or you may read it just when you need it.
The puritans used to say “pray until you pray”. I believe this might be relevant here: Keep trying to know Jesus through prayer and the Bible, until you find that it naturally happens while you do it.
I will pray that this may be real for you soon, and that you may hear the voice of the Good Shepherd, Jesus.
Let me finish picking up that question at the end: We can hear God’s voice, and his Spirit lives in us who have trusted Jesus. But until we are face to face with Jesus, sin and our old nature will be something we will continue to have to battle. Paul often spoke about this. All of Romans 8 is relevant to this. In verse 10 we read, “if Christ is in you, although the body is dead because of sin, the Spirit is life because of righteousness.” God continues to work in us, and we can know him more and more, hoping that our thoughts become gradually more in line with his thoughts, and our hearts become more and more after God’s own heart. With the help of God’s Spirit in us, we can sometimes love other people properly. And yes, in such a case, God has helped us. When we fail? It isn’t that God has made us fail, but that in that particular instance we may have followed the desires of our own flesh and the enemy. But while it is a battle, even if we fail, He remains and his love and invitation for us remain. Take heart my friend, and continue to fight the good battle trying to know Jesus and trying to follow Him. I assure you it is worth it!