Theres a lot to think about in here, but something that occurs to me is Intention Vs Happy Accident
Its a really tricky one - if youre objective is to create an imperfection or exploit a flaw in the fidelity of a given piece of gear in an intentional way, then is it not contradictory? Are you not then striving for a simply different kind of perfection, moving the goalposts within which you aim for your mixes to fall?
The way I can see, and have heard it working, is when it isnt planned. The first thing that comes to mind is in the perenial performance perfection debate. Single takes vs punched and edited perfection. I need say no more to illustrate the relvence of this, I'm sure, given that most of you know way more about engineering and mixing than me.
The other thing that occurs to me is when you simply try something new to make a sound, with certain hopes for it, but always but always it will have some property that you didnt plan. Certain peices of kit and aspects of a mix can add and interact in ways you didnt expect and the effects can (sometimes) be very desirable, if not 'by the book' (I know, what fucking book? You know what I mean). I think the 'embrace the imperfection that works' attitude can work really well if you can be prepared to run with these (sometimes) happy accidents that are not in your control, and were not planned.
The key must therefore be continual and as unprejudiced as possible experimentation, since while you can reproduce these things after you've done them once, but cannot come up with them intentionally the first time (they are after all 'accidents') youre only, it seems to me, going to find them by, in short, fucking about with whatever tools you have at your disposal in whatever fashion occurs to you. The rest is just (hahahahahahaha!) having the balls to go 'thats weird, but fuck it, I like it, it stays'.
IMO.