Does collecting saliva and swallowing it break the fast?
Swallowing collected saliva does not break the fast, but it is an unnecessary and meaningless act.
What is the ruling on wiping over socks?
It is not permissible to wipe over most common socks today because the conditions for wiping are not met. The concession was reported for wiping over leather socks (khuff) and socks (jowrab) with conditions: They must be thick, not allowing poured water to penetrate, enable one to walk in them, be worn while in a state of purity (from ablution), cover the entire foot up to the ankles (meaning covering the protruding ankle bones), and not be torn. And Allah the Almighty knows best.
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.
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.