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.

I suffer from chronic asthma which requires ventoline inhale; which is an air causes the risperatory track/airways to expand. Am I permited to use it during the daylight of Ramadan? And does break one's fast? Noting that I can't go an entire day without using it?

Taking inhaler through the mouth or the nose breaks one's fast, because it is meant to reach the lungs which are part of the coelom. Therefore, whosoever use inhalers for couple of days is obliged to preserve his fasting and make up that day later. As for the ones the ones who need to use it every days are obliged to preserve his fast and feed a poor per day and the cost of feeding one poor is estimated (60) piasters for the year (1421AH). And Allah Knows Best.  

Is it permissible for a woman whose menses exceeded (15) days to pray, fast and do what was prohibited on her to do during the latter period?

If the menses exceeded 15 days then it is deemed menstruation, and in this case she is obliged to pray and fast and to do what was impermissible for her to do during the latter period. In addition, she is obliged to make an ablution for each obligatory prayer after it's due time and making sure that impuity is removed. Finally, your menstruation period is over (Questioner) simlar to your menstruation in the previos month.

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