Your questions are way beyond the scope of this user forum for income tax and questions about tax software. Your friend needs to seek paid help from an estate or financial planner. It sounds like he can well afford that kind of advice so he should seek expert advice---not advice from strangers on an internet forum.
**Disclaimer: Every effort has been made to offer the most correct information possible. The poster disclaims any legal responsibility for the accuracy of the information that is contained in this post.**
