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 for a person, who vowed to offer two Rak`ahs (units of prayer) everyday for Allah`s sake, to do so after the Fajr (dawn) prayer?

In principle, a vow should be fulfilled as it was originally intended, and if its time lapses then, it should be fulfilled at any time because of the vow. Therefore, it is permissible to offer them after the Fajr prayer, and there is no prohibition in doing so. However, it is preferable for him to offer these two Rak`ahs at some other time to avoid the disagreement amongst the scholars in this regard.

Is it permissible for a person who broke fasting in Ramadan because of being sick to pay a ransom?

If there is hope for him/her to be cured, then he would be required to make up for the missed fasting days when he/she recovers, and no ransom is due on him/her. If his/her disease is incurable, then he/she would be required to pay a ransom for each missed fasting day, which is (600) grams of wheat, or rice. And Allah Knows Best.

Ruling on combining prayers in a marketplace due to heavy rain, knowing that some people performing prayers are customers?