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There are really three questions here.

1) Is this software an investment in your career? This is not a tax question. Forget about LBYM, if this is a good investment in your future, you should seriously consider going ahead. If not, then and only then need you worry about the tax considerations.

2) Is this a deductible expense? I would argue that it is, though some may say otherwise. It falls somewhat in the grey area because it isn't necessary for your continued employment. It isn't very likely that the IRS would question it.

3) Will you benefit from the deduction? Only if you already itemize your deductions on Schedule A, AND the cost of the software (added to other miscellaneous deductions - see instructions for Sch. A) exceeds 2% of your adjusted gross income. So, there may not be any tax inducement to purchase the software.

IMHO, question 1 is the only one that is important. Answer that one and you will know what to do.

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