The Wind Blows as the Wheel Wills

Question

The Wheel of Time turns, and Ages come and pass, leaving memories that become legend.
Legend and names fades to myth, and even myth is long forgotten when the Age that gave it birth comes again.
In one Age, called the 2nd Age by some, an Age yet to come, an Age long past, a wind rose.
The wind was not the beginning.
There are neither beginnings nor endings to the turning of the Wheel of Time. But it was a beginning.

South and eastward the wind blew,
warm, dry and strong.
Dehydrated, tired and weary
Egwene pushed herself to her limits, Rand was sure of it.
Tangled up in underbrush and vines, but she would come.

North and westward the wind blew,
South lay a land known by the travelling people.
Rand was waiting, counting minutes and hours.
Was that Perrin?

Rand felt a ripple and turned, the wind had turned. Now from the East, from Kary Qari.

His mother. Had she been there all the time?
Up, over the mountains to the north, in the city where the wind blew from?
"Kary", he shouted, but to no avail
At last, he understood. No one would come.
Born again, but all alone!

---

A good tracker can track yesterday's wind. Can you?

Hint 1:

If this puzzle sends you to Monaco then I think you might need a new courier.

Hint 2:

Tracking the wind shouldn't be too hard when you know where it's going.

Hint 3:

Maybe it would have been easier if I had spelled his mother's name differently. I suggest you use Kari or Qari instead. Let's pretend it was just a typo in the poem.

Hint 4:

You start in a city whose name is derived from [insert language here] "place of the winds" and end in a city whose name might be derived from [insert language here] "a place where wind is pounding".

Hint 5:

It should be possible to draw a simple polygonal chain / path on a map.

Hint 6:

You can disregard the first paragraph. And a lot of the other stuff is simply scenery.

Hint 7:

A big tips this time: Gareth McCaughan's guess that Kary/Kari/Qari is supposed to be read from the east is correct.

Final hint:

Relevance of hints:
Hint 1: refers to two "things" that have one thing in common. What is it, and how can it help?
Hint 2: The direction of the wind is relevant (essential) in all paragraphs
Hint 3: Assume it says Qari. (It's written differently because "names fade"
Hint 4: The starting city could not have been derived from the original puzzle, only the area. The end city could be derived from the puzzle.
Hint 5: Using Hint 2, you can draw lines on a map. (Directions are only approximate. South-east can for instance be very close to east (like 95 degrees))
Hint 6: The only (partly) relevant part of the first paragraph is "names fade". But you could solve this puzzle without this knowledge, so you can disregard that paragraph. It's to set the scene, so to say.
Hint 7: If you read Kari from east to west. What do you think will help in other paragraphs?

_{No in-universe knowledge is needed for this puzzle.}

Answer 1

Partial and uncertain answer

I'm not sure exactly how partial, because I'm not sure exactly what the question is asking nor what parts of it are clues to be picked up as opposed to scene-setting. I'm fairly confident that I have the right overall theme, but there are enough things I can't fit in that I won't be astonished if I turn out to be barking up quite the wrong tree.

I think we are looking here at

the history of the Apple Macintosh and its typefaces, with particular emphasis on the "classical" pre-OS-X Mac.

The windy city is

CHICAGO.

Kary/Kari/Qari is

not, as I first guessed, Iraq read "from the east", but Susan Kare, designer of many early Apple Macintosh fonts and icons. ... Though her name is pronounced like "care", which gives me pause.

I think the land to the south known to the travelling people might be

Egypt (the word "gypsy" is a corruption of "Egyptian", though of course that word's deprecated these days and the people in question were never actually from Egypt), whose capital is CAIRO, whose name is shared with another Kare font on the Mac. (A dingbat font, whose characters are symbols rather than letters.) I'm not very convinced by any of this, though.

I confess myself baffled by the south-and-eastward / north-and-westward blowing of the wind. My best guess is that

it's describing the geographical migration of the Mac's system font names. We start in Chicago. We head south and east to Geneva and more generally to Switzerland for which Helvetica is named. And then north and west again to San Francisco. But why the wind ends up blowing from the east, apparently from Chicago, I'm not sure.

The "Second Age" is

presumably that of the original Apple Macintosh (after the 8-bit micros like the Apple ][, but before today's OS X)

and I guess "born again, but all alone" may be

referring to the Mac OS X era, in which all those Susan Kare creations are abandoned and largely forgotten, which is why Rand's mother is never coming. -- Although apparently no one is coming, so maybe I haven't understood this right yet. Or maybe "all alone" is a reference to the fact that these days Apple have pretty much settled on their San Francisco font for everything.

Hint 1 is

pointing at the Monaco and Courier typefaces (the former is another Susan Kare creation for Apple, the latter not).

Some things I don't understand (maybe some of them are scenery rather than clues?):

• The underbrush and vines.
• The warm/dry/strong/dehydrated/tired/weary business.
• Why Rand is counting minutes and hours.
• The wind directions. (I have a half-baked theory above, but it doesn't really explain why the wind is eventually coming from the east. I can kinda fudge it, but not convincingly.)
• Some of the ordering. (E.g., I have what may be an explanation for the wind blowing "north and westward", and what may be an explanation for the southern land known by the travelling people, but I don't see why they appear side by side in the way they do.)

That's a lot of holes. Maybe the above is all nonsense. If so, then my best theory is

that Kary/Kari/Qari is Iraq read "from the east" after all, the land known to the travelling people is Egypt or maaaaybe Israel (for obvious reasons), and Rand is somewhere in the Middle East or maybe in the Mediterranean Sea. But I can't get much else to fit with that.