As you said, it's a gray area and you're probably not going to get a firm answer.
The general rule is: Educational expenses to improve your current job skills are deductible. But learning a new job is not. From JK Lasser’s Your Income Tax 2013, pg 580: "For a deduction, the courses must be related to your existing job responsibilities and not lead to qualification for a new business.
Pursuit of an MBA is a much discussed situation and is somewhat similar to yours. The tax court has allowed deductions for MBA expenses where individuals with some managerial or administrative experience took the courses to improve skills needed for their existing jobs." This doesn't come up very often because most people come out better with the Lifetime Learning credit (LLC). But you can do both if you tuition is more than $10,000. The first $10,000 of expenses qualifies you for the LLC and any excess might qualify as a business expense. http://www.forbes.com/sites/mattsymonds/2014/04/11/the-mba-and-the-taxman-claim-or-not-claim/#4e857f...
"Many M.B.A. students qualify for a deduction, however, because they have worked before enrolling in a program and are seeking to “maintain or improve” their skills, as the law requires. In addition, the degree doesn’t lead to a license". http://www.wsj.com/articles/good-news-for-m-b-a-students-tuition-is-now-more-deductible-1471013805
