We examine how financial theory and economic principles offer guidance and
predictions about the organization of investments and asset allocation decisions given the
structure of taxes in estate--planning situations. We provide insight about many of the
conventional approaches to estate planning and suggest how these strategies can be
enhanced. For example, we show that the advantage of the reset provision by which the
investor’s capital gains tax bases are adjusted to the market value at the time of death is
greater in the presence of individual rather than joint ownership of assets, provided that at
the first death of one of the joint owners the basis is reset to an average of the date of
death value and the survivor’s original cost. We analyze asset location and distribution
policies in the context of trusts that are outside of the taxable estate of its principal
beneficiary as well as direct funds owned by the beneficiary, highlighting the interaction
between estate taxation and the reset of the capital gains tax basis at death. We compare
the optimal decisions for traditional tax-deferred accounts and after-tax (“Roth”) IRAs.
Finally, we also examine the value and importance of borrowing in various contexts in
estate planning.