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.
Does ill-gotten money hinder the answering of the Du`a (supplication) and the means of subsistence?
Sins hinder the answering of the Du`a, and deprive the sinner from means of subsistence; whereas, acts of obedience facilitate making a living. Allah, The Almighty, Says (What means) : "And for those who fear God, He (ever) prepares a way out. And He provides for him from (sources) he never could imagine." [At-Talaq/2-3].
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.
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.