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.
What is the ruling when the monthly period when exceeding (15) days?
The maximum duration of menstruation is 15 days. If it exceeds this, it is considered irregular bleeding (Istihada). In this case, one must perform ghusl (Ritual bath) after menstruation, pray, and make wudu for each prayer after its time begins. She should return to her previous menstrual habit regarding duration and timing. For example, if her period used to be from the 20th to the 27th of each month, this is considered her menstruation period. Anything before or after this is Istihada, during which she only leaves prayer and fasting for the habitual menstrual days, then performs ghusl and resumes praying.
Is it permissible to offer Salah (prayer) on behalf of the sick who is on his/her death bed, and is incapable of offering it?
It`s impermissible to offer Salah on behalf of the sick, or the dead.
Is it permissible to offer prayer at home, or should it be offered in the mosque?
All perfect praise be to Allah, The Lord of The Worlds. It isn`t preferable for the man to pray at home as praying in the mosque is twenty seven times more rewarding. Therefore, this should motivate him to offer prayers in the mosque. And Allah Knows Best.