The answers I would except would describe the most popular licenses with bullet points (e.g. allows commercial use or not, viral or not etc.).
I know this is more of a wiki-type thing, but SE is somewhere between a wiki and a Q&A isn't it?
I agree with Yannis's comment that a "how to" guide would be a better blog post than a question. It sounds like the question that you described would turn into a list question, which are called out in the definition of "not constructive".
Personally, the "how do I choose a license" boils down to "read each license, decide which one best fits your need". There's no real process or methodology to explain, and there's really no alternative ways. There are some tools out there to help you find an appropriate license, but those are easily found by simple Google searches and resource requests are typically off-topic as well.
However, if you need help choosing a particular license to meet a series of needs and you enumerated those requirements in the question (and there isn't a duplicate already on the site), then I don't see why the question wouldn't be appropriate.