Without Sin?

This is a difficult one to post, as it is an incomplete understanding. More of a pondering, wanting to come to reconciliation with the truth. I have read some but not tons on the ideas of mature theologians. I invite and would love response to this thought. It is a bit of a quandry for many I'm sure.

I begin by saying, is our idea of the point at which God defines something as sin skewed? I say that because I wonder at how Jesus could live without ever telling a single lie. Even to his mother as a young child. Lying is a sin as stated in the Ten Commandments. If Jesus was a perfect child, meaning he never once lied for example, how did the community not recognize Him as special?

I also ponder how someone like David could be "a man after God's own heart." I believe that is a label given Him AFTER some really atrocious acts, deliberate murder and adultery. Is the nature of sin actually the lack of repentance, or a single act of disobedience?

I ask that question, not because I doubt that Jesus was "without sin" as scripture states, but because I wonder how it is possible even the slightest mistake could be avoided in a life of 33 years. How could he never be angry or resentful of a customer who slighted him, or common brotherly fights? Don't mistake this for some foul denial of scripture, but rather a deeper search to understand how it is possible for Jesus to be sinless, considering the way sin is defined in the world today. It is also not a lack of faith that my sins are all accounted for on the cross.

I pondered this with a friend recently, and I also recalled how Jesus was given the Spirit even in the womb. He came out of the womb fully able to commune with God. What that tells me is Jesus had the ability to recognize wrong behaviors in His life so that they never became a stronghold. Is sin really about allowing a stronghold in our hearts that separate us from God? Because that I can fathom. I believe Jesus always was in commune with God from the day of His birth.

Just some thoughts to purge my soul and seek His face with respect and patience as the answer becomes clear. I pray that He will lead me to the answer, whether through my own commune, study or that of a more accomplished saint!