I think it depends on intention.
I tend to judge according to the tools and techniques used. I've been using Photoshop since v2.5 and I try to keep up with new applications tools and techniques.
In knowing what the tools are, and methods people employ to achieve certain goals, I think it easier to see when and where these have been miss- or over-used and pushed too far.
Just spend some time on Insta drowning in a sea of texture-less super creamy characterless faces and you begin to see where everyone is going wrong in the same way.
You have a mixture of people using new tools without the experience and maturity of style (My early Photoshop work included pushing curves the wrong way for the wrong reasons), and you have the 100,000 others who do the same because someone got a lot of likes for their overly processed snapshot.
Think about Frequency separation, once it was the domain of professional level tools, the careful splitting of channels selective blurring, dodging and burning, and even then you could accidentally polish a face. The line between good and too much can be razor slim. Now it's all available in an app, at the press of a button. There is no-longer the thought or consideration taken before and at each step of the process.
Alot of it is probably down to trends, inexperience or ignorance. I think, if you are not exposed to a wealth of art, culture, language etc., and without an innate talent, you do not the breadth of knowledge or experience to judge what is good and what is too much in related fields, let alone participate at the level of an adept. Though through participation, perhaps one might hope to hone ones craft and become better with time and experience.
That said, I think comparing everything to "the Greats" as a standard is—when not being pretentious—constraining, closed-minded and, in the long term counter to originality and growth in any creative field. Lee Miller and Man Ray absolutely screwed up before codifying a process for Solarization. David Bailey and especially Rankin routinely blow out highlights, condensing their dynamic range. In other other media and Picasso broke from what was presumed correct drawing wonky faces (which I appreciate). I am not saying you can't or shouldn't learn from the " masters " but really who shoots at f/64 let alone starts a club?
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