What should a person who doubted having missed a pillar of prayer do?
All praise be to Allah, The Lord of The Worlds. The prayer of one who doubts having missed one of its pillars is valid, and nothing is due on him/her since having a doubt after offering the act of worship doesn`t undermine its validity. And Allah Knows Best.
Is it permissible to pay the expiation of an oath to a charitable party as it feeds the poor and needy such as Tkiyet Um Ali?
There is no harm on authorizing someone to handle the expiation of another to the poor and needy, since Shafiee's jurists stated that authorizing someone for the purpose of distributing Zakah, expiation and vow is permissible as stated in [Mughni Al-Muhtajj,vol.3/pp.237]. At last, the intention of the person who intends to authorize someone else suffices in this regard. And Allah Knows Best.
Which is better during the day in Ramadan: reciting the Quran or performing voluntary prayers?
A Muslim should establish a daily schedule for reciting the Quran in Ramadan.
Once they have completed their daily portion (known as a wird or hizb), they can engage in other acts of worship, including voluntary prayers (nawafil). Prayer itself is called "Quran", because a significant part of it involves reciting the Quran.
Allah says: "BE CONSTANT in [thy] prayer from the time when the sun has passed its zenith till the darkness of night, and [be ever mindful of its] recitation at dawn: for, behold, the recitation [of prayer] at dawn is indeed witnessed [by all that is holy]." [Al-Isra`/78]
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.