The "History" will be country specific, because there will typically be a delay (one year) from where the different kites R&D origins.
Also because it depends on the local "likings" in the start, and the local distributors soon after.
But what I've experienced :
1999, kitesurfing started "globally", eventhough the first pioneers had done it several years.
It was Wipika 2 lined kites, by Bruno Legaignoux, that was the "invention" and breakthrough that started everything
In 2000 things started to really "explode" in the good sense.
Kiteschools started all over, and the kites used were the Wipika Classics, and foil kites, as they were really far in development also as water foil kites.
Safety was fine as you could release to one line - but the harness line was fixed so you had to hook out yourself - but you learned that quite fast.
Bigger problem with the foils though, as if overpowered you were fu.... because if you released to a sideline, the kite would go in a powered death loop
Beside that, there where front stall problems with these foils.
But in 2000-2001 the 4 lined kites came, with both Wipika and Naish being the front runners (the only ones).
Especially the Naish AR5 HAS to get a medal for being the first really good 4 lined kite, no doubt
These kites changed everything by a huge margin, and kitesurfing was now "easy" and into a whole new level.
From now on, kites were from 3m2 up to 13.5 (and 15 or 15.5 were almost never used, but existed)
So we could kite in lots of wind, no problems.
These kites had HUGE low end, all of them, so big kites were not necessary.
Besides, the board were all directionals, so could go upwind easily and start in light winds.
From then, things changed because the TwinTips came (with the Wipika Olry being the first), and it really changed a lot of things.
The TT's became more and more sophisticated during the next years, smaller and smaller and actually just below 1 meter in lenght at one point.
And kites became "front line flyers", meaning, they could depower much more and you could hold the kite for many hours without getting tired, and they went upwind well.
The Wipika Airblast being the first, and soon everyone followed.
Big kites were NON existent.
But because the boards were getting smaller, and freestyle started to be "the thing" to do, big kites started as a "craze" almost, where one company after another started making kites bigger than 20m2, in the years 2002 to 2004
We have all been there (those who has been there from the start), and they worked fine for max pull machines for super small boards.
But they lasted VERY short.
Because, two things happened now.
Boards changed, and suddenly R&D made bigger boards (much better upwind and not requiring a huge kite) behave just as good as the smaller ones, regarding agility and freestyle.
AND, one year later, in 2005, the Bow kite came (again, Bruno Legaignoux), which REALLY changed the world !
At first, there were many "doubters", as the kites were either slow and saggy, or too much bar pressure (Takoon and Cabrinha being the first).
And they were right - the very first "samples" had some issues, that made the now very highly developed C kites (as EVERY kite till now has been) superior in general.
But it was just a short phase, till the development changed everything for 98% of kitesurfers.
Best was the first to launch a really good bow kite, "second" generation, at the right place at the right time, no doubt at all !
And every other brand, including Wipika as the "inventors" soon followed.
From then on (later than 2005), Bow kites evolved into SLE kites, which were a mix between Bow kites (quite flat kites) and C kites, but with all the advantages of Bow kites, namely huge windrange and easy relaunchable.
HUGE kites were a thing of the past now, because the new more "flat" kites had a lot more power of course, but also because boards evolved and became waveboard or bigger still agile TwinTips, and later raceboards too
The last years, I've seen no development worth mentioning though, just small minor changes, and often just to make something "new" in order to catch the eye and sell, and not because of any development really.
A major change is ALWAYS possible of course, but right now it is really stagnant IMO.
And REALLY big kites ?
Well, because of the development of bigger and better boards, they are not necessary.
But as kiteracing is huge now, the most efficient kites a bit bigger, maybe 17m2, are evolved to the max, so they are light, and goes upwind better than ANYTHING else.
And we, as users, can only say "thank you" - we get kites with loads of power, not too big and clumsy, and more efficient than ever before
PS: Maybe I've forgotten something, but I am sure I can answer