Can someone who begins a voluntary fast break it?
It is preferable for someone who begins an act of worship not to break it.
Allah the Exalted has said {what means}: "and let not your [good] deeds come to nought!" [Muhammad/33].
However, if a person starts a voluntary fast (nafl) and needs to break it, they are going against what is preferable, but there is no sin upon them.
What is the ruling on making up the regular *rawātib* (sunnah) prayers together with a missed obligatory prayer?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah.
It is obligatory to make up (qaḍāʾ) a missed obligatory prayer (farḍ). As for the timed supererogatory prayers (al-sunan al-muʾaqqatah) or the regular rawātib prayers, it is recommended (mandūb) to make them up, even if a long time has passed. Ibn Ḥajar (may Allah have mercy on him) said in his Fatāwā: "It is established in our school that it is sunnah to make up the timed voluntary prayers, by night or by day, even if congregation is not prescribed for them, whether much time has passed or little."
Accordingly, it is recommended to make up the sunan together with the obligatory prayer. And Allah Almighty knows best.
________________________________________
Note on terminology: Al-nawāfil al-muʾaqqatah (timed voluntary prayers) refers to supererogatory prayers tied to a specific time or cause, such as the rawātib (regular prayers before and after the obligatory ones), Duha, and the like. The ruling given here reflects the Shāfiʿī position.
What is the ruling on someone who intends to travel to Jeddah for two days — must he enter iḥrām from his place of residence [i.e., before passing the mīqāt]?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah ﷺ.
Whoever is firmly resolved in his intention to perform ‘Umrah before setting out on his journey, it is unlawful for him to pass beyond his country's mīqāt (the designated boundary point for entering the state of iḥrām) without entering iḥrām. If he does so, he must return to the mīqāt to enter iḥrām from there, provided he has not yet begun performing the rites of the pilgrimage — in which case nothing further is required of him. However, if he does not return, he must offer a sacrifice (sheep/goat), to be distributed among the poor of the Ḥaram.
It is stated in at-Tanbīh fī al-Fiqh ash-Shāfi‘ī (p. 71): "Whoever, intending to perform the rites [of ‘Umrah or Ḥajj], passes beyond the mīqāt and enters iḥrām only after it, must offer a sacrifice. However, if he returns to the mīqāt before beginning any of the rites, the sacrifice is waived from him."
Accordingly: whoever is firmly resolved in his intention to perform ‘Umrah before setting out on his journey must enter iḥrām at the mīqāt of his country through which he passes. Whoever fails to do so, passing beyond the mīqāt without entering iḥrām, and does not return, has sinned, and must repent to Allah, the Exalted; and he must offer a sacrifice, to be distributed among the poor of the Ḥaram. And Allah, the Exalted, knows best.
What should someone do whose gums are bleeding?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah ﷺ.
Whoever experiences bleeding gums while fasting must spit until his saliva runs clear — that is, until the bleeding has stopped — and then rinse his mouth to purify it.
If any of the blood enters his internal cavity (jawf) unintentionally, then his fast remains valid. And Allah, the Exalted, knows best.