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 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.
Does wiping over one's socks during ablution permissible?
If the socks were thick, then wiping over them during ablution is permissible so long as wiping conditions are observed. And Allah Knows Best.
Should vowed fast be offered in consecutive days, or not?
Vowed fast should be offered in line with what was originally intended by the vow-maker, either consecutively, or not.