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.
How is night prayer offered?
Night prayer is offering voluntary prayer after Maghrib and before Fajr (Dawn). As for Tahajjud, it is offering voluntary prayer at night after waking up voluntarily, and for Allah`s sake as He Says (What means): "And pray in the small watches of the morning: (it would be) an additional prayer (or spiritual profit) for thee: soon will thy Lord raise thee to a Station of Praise and Glory!" [Al-Isra`/79]. Offering Tahajjud is better than offering voluntary prayer before going to bed.
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.
Is the one who gives up on marriage because he can`t afford it considered sinful?
Marriage is desirable, but one who can`t afford it isn`t considered sinful. However, he should supplicate to Allah, and seek His forgiveness.