@djensen I definitely agree with the idea of “Play Axis & Allies Online (description will mention TripleA)”. I have been maintaining the Software section for quite some time now and I would say that 95% is about TripleA, 3% (if ever) is about the totally outdated “Hasbro CD” (actually hardly valid content), and the rest are some lonesome threads about some Apps here and there, actually without further discussion.
In this context I am not convinced that an additional category would add any value here, given that you intend to re-organize and clean up a bit.
So my idea would be to take the not very frequently and sometimes redundantly used “Player Help” category and merge it with your “Software and Tools”-idea. What is in “Player Help” today is most of the time related to software, to tools, to calculation,  etc.
I think that would match perfectly.
A merged-this-way category could be named “Player Aids, Tools and Software”, for example.