Well,given that the amount of insolvency is determined at the time the debt was forgiven, and your dates are pretty far apart, I would say you need to complete several 982 forms . TurboTax is not really set up for this, because the amount by which you were insolvent at the time of the debt forgiveness determines whether any or all of your forgiveness income is taxable, and that would have to be determined individually. i'm sure this isn't what you wan to hear but I highly recommend you go to a tax prepare who can help you with this instead of using our program this year. Sorry