James L. Musselman (South Texas) has published Federal Income Tax Deductibility of Higher Education Expenses: The Good, the Bad, and the Ugly, 35 Cap. U. L. Rev. 923 (2007).  Here is part of the Introduction:

This Article will discuss briefly § 162 and its requirements for the deduction of business expenses generally; discuss briefly the history of the deduction of educational expenses under the Code (specifically, higher education expenses); explain in detail the Regulations adopted in 1967 that deal with the deductibility of educational expenses under § 162; explain in detail each of the tests set forth in those Regulations and analyze cases that have been decided pursuant to those tests; and discuss the recent cases mentioned above in which the Regulations have been misapplied.