Is it permissible to offer Tahajjud prayer after Witr prayer?
It is permissible to offer voluntary prayer after Witr (An odd number prayer performed between Isha and Fajr) prayer. However, it is desirable that the night prayer be ended with Witr. Therefore, it is desirable for one, who thought that he was most probably going to wake up at night in order to offer Tahajjud, to offer Witr after it, but one, who fears that he might not wake up, should offer Witr before going to bed.
A woman used contraceptive pills, and her menses exceeded (15) days, is it permissible for her to fast?
The maximum of menstrual blood is (15) days, but if it exceeded that due to a medication, or the like, then it is Istihadah (bleeding outside the monthly period), and in this case she should perform Ghusl (ritual bath), pray, and fast. Moreover, she is obliged to make up for the missed fasting days which exceeded her regular menses. And Allah Knows Best.
Is it permissible to offer Istikhara prayer (seeking guidance) after Witr Prayer (A confirmed Sunnah which is offered after Isha prayer and before Fajir prayer with a minimum of 3 Rak`as and a maximum of 11)?
It is permissible to offer Istikhara before and after Witr prayer as it is permissible at any time except that in which prayer is disliked. And Allah Knows Best.
How are gaps filled during congregational prayer?
A praying person is allowed to take two steps in order to fill the gap in the row ahead. If the distance was long and requires much movement, then it is impermissible for one to move to fill it because much consecutive movement (three movements) during prayer invalidates it.