TurboTax Live is out of scope for the type of planning you are need. I would suggest working with a local tax preparer until you have everything accounted for your to-do list and then using TurboTax self-employed in the future. With TT Live, you get the agent who answers the phone. They may be very familiar with your question and able to help, or they may not have a clue and cause you more frustration.
Every time you call Live you will get a different agent and a chance that they will be able to assist you. Don't put yourself through that stress. Go to a person who knows you and will not have to start over from scratch every time you have a question.
