The author of this book—may Allah سبحانه وتعالى have mercy on him—explains: These narrations apply to those who have the choice and the ability to begin with either Mecca or Medina as they wish. However, for those who are compelled to take a specific route, starting with one and not the other due to circumstances, they do not have this choice. If they are directed to take the route to Medina first, it is better for them to begin there. This is because one should not skip visiting Medina, the Prophet's grave (peace and blessings be upon him and his family), and the shrines of the Imams عليه السلام with the intention of postponing it until their return. They might not return or might pass away before doing so. Thus, it is preferable to begin with Medina in such cases, and this is the intended meaning of the narration.
Commentary #1