There can be "active transgression" (the one who causes the rule or law to be broken); there can be "passive transgression" (someone who is involved in the breaking of a rule or law but not responsible for breaking it); there can be "ignorant transgression" (breaking a rule due to not understanding it); there can be "intentional transgression" (knowing a rule and breaking it anyway). Of these categories, generally speaking, only those that are done intentionally and in violation of one's understanding are viewed as "sins" that require direct, personal punishment. All others (the passive and the ignorant) are believed to be covered by the Atonement of Jesus. (I tend to use James' definition of "sin" in the Bible that requires knowledge and/or understanding.)
For example, a rapist is an active transgressor, but s/he also can be either an ignorant transgressor (think of a ruler who has been taught since childhood that sex is his right and refusal is not an option, living in a society that reinforces that assumption) or an intentional transgressor (the VAST majority of cases in our day and age). I understand the theft analogy that some use when discussing rape, but I don't think ANYTHING has been stolen in a rape, since I don't agree that a victim of rape has "lost her virtue". A victim of rape is still every bit as "pure" and "chaste" and "virtuous" after the rape as she was before it, specifically because she is not held accountable for what happened.
I think Jesus definitely "transgressed" while He was growing up, IF that is focused narrowly on "ignorant transgressions" - and perhaps breaking a lower law to fulfill a higher law (like ignoring his parents to stay in
That actually is the heart of this post - that there are things that occur in our lives that "technically" violate commands that will not be accrued to our "debt" simply because we didn't choose them or weren't aware of them. They are part of the package we inherited by "keeping our first estate" / being descendants of the Fall - and our job is to improve our character and multiply our talents (pursue perfection [wholeness, completion, full development]), NOT get bogged down with guilt and obsess over our "natural (wo)man" faults. Those have been redeemed already through the Atonement as part and parcel of The Fall, so our responsibility is to work to eradicate them by acquiring the characteristics of godliness that will replace them - making mistakes and transgressing along the way and repenting when we actually sin - modeling in our own flawed way Jesus' own sinless example of growing from grace to grace and in favor with God and man.