I remember looking at a photo reportage from Estonia made around 2012-2013 (the actual year is even not important, but it is important that it wasn't Soviet time, it was this century, this decade). Sadly, I can't find it any more, but I remember it to be made by a foreigner, probably on assignment. It had very strong visual language, some of the pictures were really powerful. And it had rather gloomy tone. It was well seen and well executed, the author probably earned good money for it. I would have titled it (just by the impression it left) "Small post-Soviet country trying to redefine itself as Nordic or European, rather unsuccessfully as you can see".
So the photography was good, but it didn't resonate with me. It's not like we (as Estonians) perceive life here. Yeah, we do have 12 months of shitty skiing weather (that is, gray sky and rain), we do have young smoking mothers walking with their babies, we do have ugly Soviet architecture, but still, this is not how we think of life in Estonia. Of course, you could make equally uplifting series about everything that's good here and this is being done too, by the various PR channels (which, too, have very little to do with the reality).
Back to the story I discussed. It was like a person with (probably) multiple preconceptions took a very brief tour in Estonia and tried to find a sample of every idea that he had about Estonia. You photograph something without knowing much of it and not really caring. Or even if you do care, you might not have time to go deep. It's if you walk past a house and see a cross and a burning candle and immediately label it as a house of religious people (having no idea at all who the people actually are and what they are into).
That's an outsider's view in. It can be superficial, it can be wide-ranging, it can show just the projections the imagemaker has, it can be open-ended and inclusive, but it'll probably differ from how the situations are perceived by an insider.
Insiders have their own problems, they might sometimes miss the very obvious things that can be quickly identified by fresh pair of eyes. Yet they tend to have unique viewpoint and if a broad documentary view is not must, this viewpoint tends to be much more interesting and thought-provoking. Talking about the best works - insiders' views have this depth and subtlety to them that are not (usually/probably) achievable by outsiders. Knowing the context well allows you to look past what is apparent.
These thoughts first formed in my head when I was reviewing Andrejs Grants book, but now that they're said out and written down, I'm thinking this has been the criteria for good photography for some time now.