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.
Is it permissible to listen to chants praising the Prophet if accompanied by musical instruments?
If singing, or chanting in praise of the Prophet was accompanied by a forbidden musical instrument, then it is forbidden.
What is the expiation for breaking fast due to being on a journey, or being sick, or being in a state of menstruation?
No expiation is due on the aforesaid categories, but they are obliged to make up for the missed fast. However, if any of them failed to do so while being able to, and the next Ramadhaan has come, then making up for those days is incumbent on him/her , and paying the ransom as well. 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.