Part of the challenge of picture-taking, is to convince the viewer of your point of view or perspective. It's not about being the "arteeest", but giving the viewer the necessary references points so that they "naturally" see what you see. Easily said, not so easy to put into practice. And let's not get into the sanctity of photography as a purveyor of truth - we all know that photographic skill is to present a certain perspective, eliminate from the frame everything that doesn't support that perspective, and if we can't eliminate it, then clone it out or otherwise de-emphasize it in postprocessing. This is no different from what we observe in journalistic writing, where the journalist, either consciously or unconsciously selects the facts that support a point-of-view. Or take the actions of the painter who paints a certain abstraction (emphasizing certain elements and completely ignoring others), with the goal of conveying an interpretation of the scene. Certainly, in the areas of commercial or political presentation, there is often the barest of connection between the "message" and the reality.
With respect to the imagery that makes YOU (Andrew) happy, it's your sandbox, and you do want you want (as we all do). When we start to share our creativity, then we can expect a bell-curve of reaction. If my preference is on one side of that bell-curve, then probably very few will "get" what I'm doing. If my imagery is of the type that falls smack in the middle of that bell-curve of esthetic, then lots of people will like it. It doesn't mean it's great - it just means that the reference points I use in the image are recognizable to most. And that is what I think you're referring to when you mention the sharing on Flickr.
Then there's the issue of "pretty" vs. "great" . In my view, a "great" image should provoke emotion and/or a "wow" reaction. Ideally, the image should become a window on a deeper truth, and the viewer should read into the image. What they read may or may not be what the photographer intended, but certainly, a "great" image should cause engagement with the viewer. Good photojournalism and street photography do that. Other genres of photography don't pull on the emotions quite so obviously, but I can think of many images that caused me to stop and look - really look. And then come back and look again. Now that's not to say that "pretty" isn't desirable on its own - but it's eye candy - pleasing, but not necessarily very nutritious. On the other hand, "great" pictures can also be hard pictures to look at - especially if they highlight something that the majority of us don't want to think about. Of course, not all "great" images have to leave your conscience raw and hurting - sometimes they are great because they open our eyes (and our minds and even, occasionally, our souls) to some aspect of the world.
Personally, I have a pretty clear idea of when I'm making "pretty" shots, and when I'm trying for that "stretch" image. I haven't yet made a "stretch" image that I'm really happy with (and I've been at it for more than 50 years), but that's part of the challenge. By the same token, I haven't yet written the short story that would make people change their religion or profession, but who knows...
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