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 correct point at which to raise the hands when standing up for the third rak‘ah (after the middle tashahhud)?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah ﷺ.
Raising the hands while saying the takbīr [when rising for the third rak‘ah] is a recommended sunnah, and omitting it does not affect the validity of the prayer. The proper time for this is after rising from the middle tashahhud, once one has fully stood up.
It is stated in I‘ānat aṭ-Ṭālibīn (Vol.1/P.158): "His statement, 'and rising from the first tashahhud' — meaning, this manner [of raising the hands] is also a sunnah when he rises from the first tashahhud, that is, when he stands upright from it.
Consider [the question]: when precisely does the raising of the hands begin? Is it at the very start of rising from the first tashahhud, or after he has reached the minimum position of rukū‘ [i.e., once fully upright]? The apparent, [correct] view is the latter — even though the outward wording [of the text] might suggest the former — because at the very start of his rising, he is still relying on both hands [to push himself up, and therefore cannot yet raise them]."
It is stated in ‘Umdat as-Sālik (p. 53): "If his prayer extends beyond two rak‘ahs, he sits after them in the iftirāsh position, recites the tashahhud, and sends blessings upon the Prophet ﷺ alone, without [mentioning] his family [at this point]. He then stands while saying the takbīr, supporting himself with his hands; and once he has stood upright, he raises them level with his shoulders." And Allah, the Exalted, knows best.
Is it permissible for a sick person to pray while sitting on a chair?
All perfect praise be to Allah, The Lord of the Worlds It is permissible for a sick person, who is unable to stand up, to offer prayer while sitting on a chair. If he/she was unable to prostrate while on the chair, the he/she should pray while sitting on the ground, but if he/she was neither able to bow (Roku),nor to prostrate, then he can do them while sitting on the chair. And Allah Knows Best.
Does the use of suppositories, enemas, or hemorrhoid creams affect the validity of fasting?
Enemas and suppositories inserted through either of the two private passages invalidate the fast. This ruling is based on the statement of Ibn Abbas (may Allah be pleased with him): "Breaking the fast occurs from what enters (the body), not from what exits." [Reported by Al-Bayhaqi in As-Sunan Al-Kubra]
His generalization regarding anything entering the body indicates that it invalidates fasting, whether it is nutritious or not, as even non-nutritious substances resemble food in form.
It is recommended to use them before Fajr or after Iftar. However, if a person must use them while fasting, they should continue refraining from food and drink for the rest of the day and make up for that day later.