Is it permissible for a man to wear transparent clothing?
It is not permissible for a man to wear transparent clothing that reveals his 'Awrah (the area that must be covered). The 'Awrah of a man is "from his navel to his knees", and modesty is more prudent. And Allah Knows Best.
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].
I missed fasting 30 days of the obligatory fast within the last 6 years and 20 days. How do I fast? And what should I do?
Missed fasting days must be made up, and it is permissible to make them up on non-consecutive days, as continuity is not required for making up missed fasts. Additionally, expiation (Fidya) must be given: feeding one needy person for each day if the makeup is delayed for one year. If the delay extends to two years, Fidya must be given to two needy people per day, and so on. 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.