Is it permissible to repeat the Istikhara (seeking guidance) prayer, and is it a condition that one should sleep after offering it?
All perfect praise be to Allah,The Lord of The Worlds Istikhara is offered once, but it is permissible to repeat it, and sleeping after offering it is not a condition for its validity. And Allah Knows Best.
What is the ruling on someone who vowed to fast for two consecutive months, but failed to do so?
He is obliged to fulfill his vow by fasting for two consecutive months, but if he fails to do so then, it remains a debt on him until he either fulfills his vow, or dies. In case of his death, his guardian is supposed to fast on his behalf, or donate food from his estate in return for fasting, but if the guardian fails to do so then, it is all in the Hands of Allah.
What should a sick person, who is incapable of fasting, and who didn`t make up for missed fasting days, do?
One who has missed fasting days is obliged to make up for them, but if he/she wasn`t able to because of an incurable disease , or old age, then he/she has to pay a ransom which is feeding a needy person for each of the missed fasting days. And Allah Knows Best.
Is it permissible to openly announce the engagement of a woman who is in her waiting period (iddah)?
It is not permissible to openly announce the engagement of a woman in her waiting period (Iddah), but it is permissible to hint (imply) at it if she is in her waiting period after the death of her husband. And Allah Knows Best.