That's exactly the thing that I think -- for me, at least -- helps to differentiate my reaction to these things when I see them. A lot of it relies on how I interpret the artistic intent. If it feels organic, or in service of the overall artistry, that carries a different feeling than if it feels like a manufactured artifact of a commercial project. Does it feel like it's in service of a larger idea, or is it a hollow means to generate publicity?
It's not a science. I can't read artists' minds, nor can I entirely separate my reactions from my preconceived notions of who these people are.
It also doesn't escape me that a lot of this is probably inextricably linked to genre, and by extension to gender politics. Women will undergo more scrutiny than men will. Is she being too sexual/not sexual enough? Is she being too edgy/chaste/intense/disaffected/gay/smart/whatever? Bowie and Prince are two great examples, but there aren't a lot of male artists doing the same thing right now.
That said, here's my "hot take." I think The National has gotten way too precious about the aesthetic choices surrounding their last few albums. The imagery for Sleep Well Beast and I Am Easy to Find felt forced and cynical, to me, almost to the point of impeding my ability to absorb the albums on their own merits.