Andrew Blair-Stanek (J.D. 2008, Yale) has published Note, Using Insurance Law and Policy to Interpret the Tax Code’s Loss and Medical Expense Provisions, 26 Yale L. & Pol’y Rev. 309 (2007).  Here is the Conclusion:

Insurance law and policy have developed over centuries at the hands of innumerable judges, legislators, and regulators. The practices of the insurance industry have emerged from the input of these government actors, as well as from scholars, consumer groups, and data on literally hundreds of millions of policies. Insurance case law provides well-reasoned, policy-oriented resolutions to a wide variety of situations and problems in the tax context. In interpreting and implementing the partial insurance programs of §§ 165 and 213, the IRS and the federal courts have much to gain from looking to insurance law for precedent and guidance.