You shouldn’t worry about the repetition of the “Hail Marys”, or on saying the Rosary perfectly (as if you skip a prayer, or add one too many) The focus, through the repetition of the prayers, is on the mysteries. For instance, The first sorrowful mystery is Christ in the Garden of Gethsemene. Focus on his fear. Fear of death, pain, and his fear of his perfect sacrifice not making a difference in the world. What are your own fears? Anxiety is something we can all relate to. Fear is something we all go through. We are similar in the fact that Christ was a man and human. I have to align my sufferings with those of Christ in order to truly understand them. When I do, I discover something new, something about him I hadn’t thought of. I don’t think we need to focus on the picture in our rosary book and try to meditate on that frozen image. I think we need to walk with him as a man, and kneel beside him as he suffers. Hold his hand. Imagine that. Help him to get through a night of internal suffering, stay awake with him as the disciples did not. I think I have learned much from this, and still do. If you have trouble identifying, try reading descriptive texts on the events/mysteries. The Poem of the Man God has great descriptions of the passion. But there are numerous books by saints as well, that describe Mary’s obedience to God as in the Joyful Mysteries, or about the Resurrection, as in the Glorious Mysteries.
Paint a picture for yourself and it will be easier. Certain mysteries still elude me and sometimes I am quite distracted, but as in the other responses, we have to perservere, and just offer it up.