David H. Schnabel (Debevoise & Plimpton, New York) has published Revisionist History: Retroactive Federal Tax Planning, 60 Tax Law. 685 (2007). Here is the Conclusion:

The fact that there is any room at all in our tax system for retroactive tax planning is somewhat of a gift, and suggesting that the law be liberalized is somewhat like looking a gift horse in the mouth. However, having a clear set of rules of general application upon which taxpayers may rely would seem to benefit both taxpayers and the Service alike. Accordingly, it would be appropriate and helpful for the Service to issue a published ruling upon which taxpayers could rely that reflects the issues addressed in the recent private rulings dealing with rescission. In contrast, the Service seems well justified in limiting the ability of taxpayers to modify their prior agreements and in resisting taxpayer efforts to use state court proceedings as a back door way of altering the federal tax effects of their transactions.

It seems appropriate that the greatest opportunity for retroactive tax planning exists under the check-the-box regulations since the area is governed almost entirely by federal tax regulations and the Service is therefore in a strong position to police exactly what works and what does not work. Although this Article has identified a variety of questions that arise when engaging in retroactive check-the-box planning, this aspect of the regulations (that is, the ability to change classifications retroactively) seems to have functioned fairly well since the regulations were first adopted. Moreover, because the entire area is governed by federal tax law, tax advisors are generally well equipped to discern answers to the questions on their own. That said, definitive answers to the questions raised above would be welcome.