No doubt there will be a little bit of luck involved; you have to hit the right segment of the community in the right mood on the right day with the stars aligned just so, and that's if the question is well-formulated, interesting and answerable.
Of your two example questions, the first ("Is there an 'Ansel Adams' of urban landscapes?") I would mark as essentially meaningless. There is a trivial interpretation, which is to ask if any photographer has ever been granted such a lofty title by a writer or critic such that it stuck well enough to be searchable on teh intarwebz. If there is a unique and definitive answer, knowing it won't add anything to the community, any more than knowing that Harold Edgerton's friends called him "Doc". If the question is asking whether anyone has ever applied the Zone System (or its digital spiritual descendant, HDR) to cityscapes effectively and without extra cheese, the answer is "of course", and may come with a few example links to any of the thousands of photographers who've managed the trick. It could be specifically about making the Chrysler Building look like Half Dome, or geometrically abstracting neoclassical or Modernist architecture in a manner similar to Adams' treatment of adobe structures. Or it could be asking if anyone sparked a popular vision of Gotham in the same way that Adams did for Yosemite.
On the other hand, the "same" question, asked backwards, might be interesting. If you start with a photographer and ask why he might have been widely called "the 'Ansel Adams' of urban landscape", that can lead to a cogent expository on similarities in artistic and technical approaches, the effects the photographic work may have had on tourism, immigration patterns or preservation efforts, etc. But the key to both the question and the answer(s) would be applicability rather than a mere history lesson.
The second example question ("Why do people say Dan Winters breached the gap between commercial and fine art photography?") is more definitively answerable, at least insofar as it concerns his celebrity portraiture. It's still subjective as all-get-out, but at least it touches on familiar territory for a technically-minded crowd (taxonomy and nomenclature). (I think the answer is too obvious to have asked the question, but I can sort of see why it might be asked by someone else.)
Photography lives in three disparate realms: science, craft and art. Because of the history of the Photography stack, it's not at all surprising that we have a lot of members who are fascinated by the science aspect. (It's fair to say that most of the early members got here via the footer or sidebar on another Stack or through Area 51. People who discovered the site as a stand-alone photography site came much later.) Honestly, though, most of the science of photography lives at a level below the level of abstraction we are working with. In my photographic lifetime, that level of abstraction has been raised tremendously. (In computing terms, when I was a kid, it was like working in C with frequent drops to assembly. I didn't have to know how to make the gates, but I did have to know how to twiddle bits in order to get even the most basic stuff done. Today it's more like Python or Ruby, and you can spend most of the time living happily in the Django or Rails world without even dropping to the base language, let alone building your own optimized binaries.) But the science part is full of numbers and charts and things that make tech-heads' worlds comfortable, and gear questions are a good proxy to that world.
The art aspect may live at a level above what we can comfortably deal with. It's tremendously subjective, and it tends to divide people into two opposing religious camps, which for convenience's sake I'll label the Buddhists and the Pythagoreans. There are masterful photographers in both camps; the only real difference between those masters is in the way they articulate and justify the subjective artistic decisions they've made. The Pythagorean will invariably put numbers to it, no matter how bad the data fit might be; the Buddhist will go out of his/her way to deny the existence and meaning of numbers even while invoking at length a "natural harmony" that can be concisely described as "the Fibonacci sequence". A Buddhist critic will find what he's looking for in a Pythagorean's photograph, just as a Pythagorean critic will find his colour tetrads and Golden Section overlays work just fine on a Buddhist's photo (perhaps with some data-fitting problems). The only definitive answers or magic recipes that exist result in things like school pictures, where nothing is wrong, but nobody cares.
This site should be primarily about the craft; about using the technology to translate the vision (whatever that might be) into a tangible, finished photograph. There are far too few substantial "how" and "why" questions that don't involve post-processing (or Social Engineering for the Autistic 101, in the case of people pictures). If we're going to bring photographers into the question space, we ought to be asking about, and giving answers based on, aspects of the craft first and foremost. (We had a question that basically ran, "I hate this picture, so explain why it's art." The popular answer didn't fit with the asker's preconceptions — it didn't say, "you're right, it's an invalid expression of an invalid concept, and therefore anyone who likes it is insane" — and things got, um, unpleasant.) If we stick mostly to, "here's what I want to say, now how do I say it?", much education and edification will be had by all.