How may an Umrah performer deal with the hair on his head (by shortening or shaving) when performing three consecutive Umrahs (one for himself, one for his deceased father, and one for his deceased mother) within ten days, and is it permissible for him to don the Ihram garments from the hotel in Madinah and then enter into Ihram from Abyar Ali?

Repeating Umrah during a single journey is permissible, though refraining from it is preferable. If you perform Umrah for yourself, shaving the head is better, but if you only shorten the hair, that is permissible, and after shortening, you can assume ihram for a second Umrah. However, if you shave your head, it is preferable to wait until hair grows back sufficiently for you to shave it in the second Umrah, such as ten days. If you shave your head and wish to perform Umrah but no hair has grown back, it is recommended to pass the razor over your head. There is no harm in wearing the ihram garments before the miqat and entering into ihram at the miqat.