This is going to be a bit murky as I can't quite define a way of thinking about it and therein lies the problem.
Let's take the questions "What is the best cloud IDE?" as an example.
Codeenvy is good, among other things, because it is easy to set up and has a powerful editor.
Now, how can I back my claim of easy setup? Well, it's because for an average user it takes around 2-3 minutes to get started. And for collaborative projects there's Environment Factories that, after setting up once, take as much time as opening a URL.
But the Environment Factories, although closely relate to ease of use, is a powerful benefit containing a lot of features all by itself. Should the description of my claim contain those features as well or should I write Environment Factories out as a separate pro and list the features/benefits there?
Now it's two pros overlapping each other, or a single pro with a very valuable description that might get overlooked because of it's length, or a single pro/con with a less valuable description.
From this use-case I'd say splitting those into two with little overlap makes sense. But then...
What about my claim of having a powerful editor? There are multiple reasons why I may make such a claim, there's is a long list of features there. If I list them all in the description, they drown in the noise - there's no real reason except for "has a lot of features". If I list them out each as a separate pro, I'll flood that section and maybe after voting the good reasons will float up, but does that help me make a choice? And, also, then there's some overlap between those features so now there's the same information countless times.
Currently, it's case by case, but it would be nice if there was a way of thinking about it that made it clear and as a result could be adopted site-wide.