The Philosophers' Cocoon

In our September "how can we help you?" thread, a reader writes in:

I am a second-year M.A. student of Philosophy at a low ranked university, looking forward to applying for another master's next year in a better university. I passed nine graduate philosophy courses with good grades. My bachelor studies were not in Philosophy and I had just one Philosophy course at bachelor, so I think I need my master's degree (and courses) for a successful application to a philosophy major. I have no personal problem completing my current studies as a master student to get my degree, but there is an educational law in my country that prevents people from entering master studies twice unless the mandatory military service (which lasts two years) is completed. I can withdraw from my current M.A. and apply for another M.A. without any problem with this law. In that case, my current university will give me an official transcript, but no degree. I prefer this withdraw option because it saves two years for me. Are there any problems with the withdrawal from my current master's in applying for another master? I mean does this have a bad effect on the strength of my application, and should I mention this in my application? Thanks for your advice.

This is an interesting query in a couple of respects. First, it raises questions not only about what this particular poster should do given their situation. Second, it raises more general questions about what people should do–both in graduate school applications and in job applications–regarding similar 'oddities' on their CV.

What do you all think? First, what do you think this reader should do? Do you think withdrawing from one MA and applying to another will give them problems? If so, what's the best path forward for them? Should they try to explain their situation in some way in their application? And how, more generally, do you think applicants should handle similar CV oddities? (If you have a CV oddity yourself, feel free to share it and/or how you handled it in the comments section!).