The point in saying that Jesus is lowly is that he is accessible. For all his resplendent glory and dazzling holiness, his supreme uniqueness and otherness, no one in human history has ever been more approachable than Jesus Christ

Jesus Christ is closer to you today than he was to the sinners and sufferers he spoke with and touched in his earthly ministry. Through his Spirit, Christ's own heart envelopes his people with an embrace nearer and tighter than any physical embrace could ever achieve. His actions on earth in a body reflected his heart, the same heart that now acts in the same ways toward us, for we are now his body. (p. 33)

It is in "our weaknesses" that Jesus sympathizes with us.

All of our natural intuitions tell us that Jesus is with us, on our side, present and helping, when life is going well. This text says the opposite... It is in our weakness that Jesus sympathizes with us.