An apt metaphor! I guess for me, I consider the 'hazy memory of what the final image should be' an outline so I wouldn't say I'm in the writing lands devoid of outlines, but it's also not really a plan since getting an idea of the overall image isn't Step 1, and also I keep realizing throughout the process that I misremembered the image; 'was it a tower? ...no it was a castle actually. Yeah, it's definitely better as a castle'
I also tend to iterate arcs of my story (which is probably about the same length as a short story if that's what you write as opposed to serials) many times XD My reason's different from yours though; I don't write things in one sitting and consider it 'finished' once I get up and close the file - my reason for iterating is more like 'oh, I was building a tower, but wait I actually want it to be a castle so I have to redo the foundations of this thing and maybe salvage a few little pieces if I'm lucky'
Consequently; I almost never ask for a second pair of eyes because by the time they've read it and gotten back to me with feedback, I would've already spotted things to change and overhauled a bunch of stuff, rendering their feedback obsolete, which would probably annoy them and be super awkward :'D
I don't think going through a bunch of iterations is something you need to improve on though! People who edit instead of rewrite the whole thing from scratch make far more than 3 edits, so the overall amount of rewriting you do comparatively probably ends up being about the same