A simple question. Yahoo is down and lacking leadership, Microsoft needs to expand its footprint. Bing has not been the answer and maybe Yahoo can help. "Given the wide reach of both Microsoft and Yahoo independently, a singular entity would already come with a great degree of demographic overlap."
And that is the challenge facing Microsoft in any of their efforts. They have become corporate while entrepreneurial technological companies take risks and push new ideas. Microsoft needs a leader. It is what Steve Jobs was for Apple. He was a visionary, a risk taker, an idealist, who sought to "think differently" and follow his gut. Without him, the challenge for Apple is to enable that same sense of entrepreneurship and risk. For Microsoft, current leadership has not led by example, they seem to simply follow.
So while a Microsoft-Yahoo merger could provide some synergies, it comes with many challenges too. It would require new risk taking to succeed. Otherwise, it will be noted as another failed attempt by Microsoft to get beyond their Windows and Office product line.
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