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
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.