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.
Should missed Sunnah prayer be made up?
Making up missed voluntary acts of worship is from Sunnah.
Is it permissible to say: "O Allah, by the status of the saints and the righteous, and our master Muhammad, peace be upon him, grant us the ability to reach Ramadan"?
What is mentiond by the righteous predecessors that they used to say: "O Allah bless us in Shaba'an and Rajab and give us the ability to reach Ramadan." [Shoa'ab Al-Iman/vol.3/pp.375]. And Allah Knows Best.
What is the ruling on having a second congregational prayer in the mosque?
All perfect praise be to Allah, The Lord of The Worlds, and may His peace and blessings be upon our Prophet Muhammad and upon all of his family and companions It is disliked to have a second congregational prayer in the mosque which isn`t visited by travelers like the neighborhood`s mosque, and which has an appointed Imam, save with the latter`s permission. Nevertheless, if the mosque is visited by travelers, it is permissible to have a second and a third congregational prayer, whether it has an appointed Imam or not, or whether he permits that or not. And Allah Knows Best.