Question #1: How much money do you need to make to benefit from itemizing your return?
There actually is no income range that will determine whether you would benefit more from claiming the standard deduction or itemizing your return. It all depends on how many deductions you qualify for. Add up the dollar amount of all the deductions in which you would qualify and if the total is higher than the standard deduction, you should itemize your return. If it is lower, then you should claim the standard deduction.
Question #2: I am in the process of filing bankruptcy. Will I need to include the resulting canceled debts on my tax return next year?