What is the authenticity of the supplication: "O Allah, bring it upon us with blessings and faith, safety and Islam, and success in what You love and are pleased with. My Lord and your Lord is Allah"?
On the authority of Talhah Ibn Ubayd Allah (may Allah be pleased with him) who reported that the Prophet (PBUH) would say when he saw the crescent moon: "O Allah, let this moon appear over us with blessings and faith, safety and Islam. My Lord and your Lord is Allah."
This was narrated by Tirmidhi (Hadith no. 3451), who said: "It is a Hasan (good) Hadith."
And Allah The Almighty Knows Best.
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.
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.