First, I want to say that these are totally legitimate objections to hold to the piece, and sorry it's taken me so long to get back to this to respond to you Raven. I haven't been feeling quite myself, and the computers I usually use have been out of reach, leaving me just my phone and... well, that's a pain in the ass to try to respond to in a large multi quote post.
Okay, so, I like this as a little slice of time/small moment thing, but I wonder if there's actually enough of a story here for this to be canon.
This concern is certainly one that sort of bears scrutiny. Even for microfiction, this doesn't say much, but the primary purpose of this piece was honestly more to inform than to expand. Quite simply put, neither Gale nor Aamir have physical descriptions actually
IN the archives. Aamir doesn't actually have ANYTHING in the archives for that matter. So the purpose of this piece was to actually lay these details out in canon so that they WOULD be canon. It's admittedly a bit of a shallow reason, but I think it's important enough to warrant... well, maybe you can't call this a story, but at least an entry.
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Honestly, the timeline bothers me less than the question of what happens to these two afterwards. The piece hints that they have divined one another is a 'walker. But the story does not give us an indication of what that means for Gale's larger arc, and if the intention is that Gale will continue, for a bit, to be unaware of what it really means to be a planeswalker or how planeswalking is accomplished, it just seems to me that Aamir's character is one who would want to help with that.
So, even if this ends up taking place after "Winds of Change," which I can certainly accept, are we to assume that Aamir simply left, or that he's signed on with the already over-crewed ship? It begs an interesting question, of course, of what Gale would do if forced to choose between the ship she just signed on with and learning how to get home.
You have done a pretty good job of fathoming (hehe... nautical humor) Aamir's character, but I think part of this is to consider the larger ramifications of what Aamir was doing as well as Gale. As far as ships crossing in the night, that can certainly be true of this interaction, but there is nothing stating that it is the finale of their acquaintanceship (hehe... ship).
I suppose it's a situation where I've had a detail tucked away in reserve since Drifting Lights and just never had a chance to actually do anything with it, but Aamir has a tendency to gift people he meets with some way to reach him. Usually a small little trinket, maybe one that they could wear on their belt, but one intrinsically tied to his magic and possessed of a spirit that can reach him should they need him. In essence, he gives them
a pager to keep in touch.* (I hope you appreciate that Raven because I set that up as hard as I could.) While I could have actually shown this, I feel like where it ends is a natural place to let the screen fade to black, and any sort of skip over her story would disservice the rest of it.
So, while the two may part, it doesn't mean that they cannot talk with each other at a later time should Gale need something. And after hearing her tale, I do feel that Aamir would be very moved for her to have proof that someone out in the grander multiverse has her back if it is ever against the wall. After all, Dominia can be a stern port fore and starboard.
*Which, it is completely up to Orcish to use or not.