I've just typed all this out once before, and as I was about to post it, the electricity cut out and I lost it all... Boy am I angry!!!
The Court cards Crowley created were based on the cycles he found in many legends and stories from arund the world, namely the legend of Percival/Parsifal in the Arthurian sagas. The Courts do indeed represent a cycle of personaes, and the main players in this cosmic drama are:
Princess
Prince
Queen
Knight/King.
In the cycle, the Prince is without a kingdom, and in order to gain a kingdom he must first win the hand of a Princess (Aladdin springs to mind here!). In most stories of this kind however, the Prince finds that the Queen is in opposition somehow and tries to stop this happening (Cinderella, Snow White), and only when he has overcome the Queen is he able to marry the Princess. When the Prince and Princess marry, they become King and Queen, and their children become Prince and Princess and the cycle starts all over again. In this cycle, we get a bit of the Heiros Gamos thing going on.
This is seen in the Percival legend. Percival's mother tries to prevent him from becoming a Knight (Notice how the Thoth King is actually a Knight!), and he overcomes her opposition and manages to become a Knight. In the opera Wagner composed 'Parsifal', which Crowley was heavily into, Parsifal fall sin love with a woman who's name I have forgotten and finally marries her.
So, that's the cycle thing with the Thoth Courts. Crowley also associated each Court with a part of the Tetragrammaton (Fourfold name of God):
Knight/King: Yod (Fire)
Queen: Heh (Water)
Prince: Vau (Air)
Princess: Heh (Earth)
I like your insight about the Princess representing Assiah and the Prince awakening her out of it. This would make sense given that the Princess is the Earth part of the Tetragrammaton and she is associated with the number 10 and therefore the sephiroth of Malkuth on the Tree of Life, which represents the earth. Also in many legends and stories it IS a Prince who awakens a Princess, either physically out of sleep or in some other way: See Aladdin, Snow White, Cinderella, Lancelot and Guinevere, and Sleeping Beauty.
Myself, I'm not a Hermetic magician and know it's not really for me, so I won't be performing any rituals to achieve knowledgel of my HGA. But my best friend is a Thelemite (Crowleyan Hermetic magician) so we regularly have discussions about all this.
Kiama