Firstly: Entering Mecca from its highest point and leaving from its lowest point
It is mustahabb that one in ihram enter Mecca from its highest point [1006] From the mountain of Kada’, at the highest point of Mecca, from which one descends to the graveyard. and leave it from its lowest point [1007] From the mountain of Kuda, at the lowest point of Mecca, near the mountain of Qu`ayqi`an. if this is easy for them. Otherwise, they may enter from any road they desire. [1008] Al-Albani says: “He should enter from the high point which today hosts Bab al-Mu`allah, for the Prophet ﷺ entered it from the highest hill (Kada’) that overlooks the graveyard and entered The Mosque from Bab Bani Shaybah as this is the closest route to the Black Stone. One may enter from any route they desire.” (Manasik al-Hajj wa al-`Umrah, p. 18) This is by agreement of the four schools of jurisprudence.